“Are we in business?”

Your sale hangs in the balance.

You’ve mustered your favorite closing question. The tension is palpable. And you’re secretly praying you’ve done enough to get an enthusiastic “Yes!” from your prospect.

You’re sitting at the culmination of your entire sales process. You’ve done your best to make the customer conversation pleasant. You’ve built up value over the five prior meetings with Pat. He’s confessed his pain to you. Was emotional about it. And even quantified it. Getting his hands on your AI software would mean he wouldn’t have to hire five additional accountants over the next year.

And yet, you’re not 100% sure he’s moving forward.

Over the past decade, hundreds of founders and startup operators have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the series unfolding in the coming weeks, we’ll cover the essentials needed for a sturdy sales process, and the factors to consider when you go about designing it. You’ll walk away with the necessary tools to start engineering your process from scratch, and the things to look out for as you take it to market for refinement. So sit tight. Tune in. And, as always, be loud with your questions. Here’s your fifth installment.

This week, we’ll focus on what comes right before asking for the order: the proposal review.

Strike out at this point, and an entire customer conversation is for naught. You’re left empty-handed. Nail it, however, and you’re bringing home the bacon. Celebratory Veuve-Cliquot is in order.

With all that at stake as you’re nearing the goal line, how does one go about designing a proposal review that closes deals?

There’s a ton to consider. So where do we start?

Well, the first thing I like to establish or remind the prospect of is the value that’s being created by my product or service. And there’s no better way to do that than a value creation/ROI slide (see below).

Before you hit your prospect with the tab, it’s a great idea to remind them what they stand to gain from the purchase. You want that calculation to be as simple as possible, so as to be easily digested by your audience. Frame it as a Before and After, as it’s done in the above slide, and your product will stand out as having a huge impact on their world.

As for the return on investment, you’re going to be at 3-5X at the very least. If you can be closer to 7-10X, that’s great. And being 10X and above makes things much easier on you.

A quick aside about ROI. It can feel like pie-in-the-sky to your prospects. So you’re going to ground it in truth and make it believable to them. More often than not, as sellers, we can get antsy at this slide and not spend enough time on it. You’re going to want to present it and linger to engage with your prospect. Throw questions out there. “How is this landing with you?” or “Anything you disagree with here?” are great to use after you’ve gone over this part.

Now, why is that?

Well, the trouble with the ROI or Value Creation slide is that prospects might not agree with what you’re showing but never voice it openly. They may not fully understand what you mean in your calculation, but they never admit it out loud. Their eyes might glaze over. Or they might nod along passively. It’s critical they’re fully bought in before hitting them with commercial terms. Without that, you’re running a huge risk of them not moving forward. As it will be hard to justify your price or defend your product’s value.

If you get a “This makes a ton of sense” or “Yes, feels totally right to me”, you’ve got a good indication as to whether the prospect’s buying into your value justification.

It’s now time to move things along to your commercial presentation. Our next slide: Pricing/Commercials (example below).

This slide is crucial as it lays out the terms for the commercial relationship. Those need to be explicit and crystal clear. So they can fully grok what they’re getting themselves into if they end up signing on the dotted line.

I love to invite questions after I’ve gone through this one. I might ask twice, just to make sure things have landed and left no stone unturned. A “Might sense?” followed by an “Any other questions on this?” might just do the trick here. If there are no questions, I’ll tell myself to stay vigilant for what comes next.

Last, but certainly not least, our Next Steps slide (see slide below).

This one has a dual purpose. One: we want to make the prospect feel like they’ll be fully taken care of as they become our customer. White-glove onboarding. Red carpet rolled out. The whole nine yards. You can do that by providing enough training. Or thorough onboarding that gradually takes the training wheels off of your product.

You’ll also want to ensure they garner value promptly after signature. Remember: the customer is placing a bet on your product. They want to know they’ll be able to exhale quickly as they begin tasting your product’s value in a matter of days. Not months. Another way you can make folks feel special is by giving them a sense that you’ll be shouldering most of the onboarding load. The Commitments section is the perfect place to illustrate that. You can have a few commitments you’ll want to see from your customer. But you’re going to want your list to be much longer than theirs, ideally. As shown above.

You might say, “Paul…you talked of a dual purpose for this slide…you only gave me one…are you shortchanging us?”

I wouldn’t dream of it. The other raison d’être for the Next Steps slide? To confront the prospect with the reality of becoming a customer of yours. It’s rubber-meets-road time. An opportunity for them to try on the outfit of being that customer.

Does that outfit feel soft and comfortable like cashmere? Have a scratchy elbow? A hole in the sleeve that needs to be sewn up?

You want the prospect to make that cognitive shift. And see how it feels. If everything feels great, you’re probably in the clear and can move to your closing technique of choice. If the outfit feels off in any way, however, that’s an objection that’s being surfaced. One you’ll have to handle.

In essence, you’ve got yourself a closing slide. The transition from tire-kicker or window-shopper to customer forces the prospect to really consider all the implications of moving forward and signing on with you.

If objections come up, great! You’re addressing key issues that would have prevented you from securing the order. If nothing comes up, then you can move in for the close.

All in all: three slides. A streamlined design of a good proposal review call or meeting. Executed properly, more often than not, you’ll hear this as you ask for the order, “Of course we are! Excited to partner with you guys.”

We’re done for this episode. Next time we get together, we’ll drill into what makes for a good onboarding sequence for your customers. Remember: your sales process doesn’t end at a John Hancock on a contract. It ends when your customer starts deriving value from your product. Thus, the significance of handholding your customer till they get there. Ciao for now.

Have you ever looked at reviews for restaurants you’ve already been to? Am I the only weirdo who does that?

I know I’m an oddball. But humor me and go do it.

You’ll find a few surprises, I’m willing to bet. I’ve always been dumbfounded by some of the reviews I land on.

“This omakase was not worth the money and I was still hungry leaving the restaurant.”

“The waiter we had was snooty and the pasta lacked flavor.”

My experiences at those restaurants couldn’t have been more different. The reviewed sushi spot was one of the best I’d ever been to. And the described Italian place delivered an elaborate pasta tasting menu at their chef’s counter.

Over the past decade, hundreds of founders and startup operators have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the series unfolding in the coming weeks, we’ll cover the essentials needed for a sturdy sales process, and the factors to consider when you go about designing it. You’ll walk away with the necessary tools to start engineering your process from scratch, and the things to look out for as you take it to market for refinement. So sit tight. Tune in. And, as always, be loud with your questions. Here’s your fourth installment.

What I’ve come to realize over the years is that people’s opinion of the same product or service can vary wildly. It depends on the lens through which they look at life. Their relationship to money. Their current mood. The quality of their day leading up to the experience.

What some interpret as pretense, others consider elegant. What some view as refined, others see as finicky. What some experience as delicate, others miss altogether.

My point? When we rely on people’s feelings to define success, we don’t get a singular view of the same experience. We get a wide variety of different perceptions.

Which is a problem. Especially in a pilot or free trial.

Last week, we talked about controlling the sale. Selling the next step. The Account Optimization Call as a forcing function. Arming your champion when you can’t be in the room. All of it driven by the same north star: tightening the screws everywhere you can, because variance is the enemy of repeatability.

This week, and next installment, we’re zooming in on two of the highest-leverage moments where founders quietly hand control back to the prospect. Today: pilots and free trials. Next time: the proposal review.

Let’s get into it.

Driving the Success Narrative

Here’s the trap most founders and startup operators fall into. The prospect makes it into a pilot or a free trial. They’re excited. And the founder — wanting to be customer-centric and helpful — asks some version of, “What would you like to accomplish during this pilot?”

Sounds reasonable. Collaborative, even.

And yet, it’s a disaster.

Because now you’re back in the restaurant review section. You’re asking ten different humans, with ten different lenses, ten different relationships to your problem space, to define success. And they will. In ten incompatible ways.

You’ll find yourself contorting yourself, trying to satisfy a kaleidoscope of expectations. Some achievable. Others regrettably not. Some on-product. Others off.

Not a role you want to play.

You want to be the one defining success. Not asking the customer to define it for you.

Flash back to early Whitetruffle

After Mike Morrell’s advice on keeping our motion lightweight. After I’d instituted the Account Optimization Call as a forcing function to get qualified prospects onto the trial. We’d gone from two-thirds of qualified prospects ghosting the signup link, to most of them showing up and getting onboarded.

I set my sights on a new problem I was now facing down-funnel.

I had qualified prospects on a 14-day credit-card-activated free trial. And I needed them to convert. Automatically. Through the magic of credit card processing, on day 15, if they were satisfied.

So I asked myself: ‘How do I make sure we convert a large chunk of trials into paid customers? How can I set expectations? Expectations we’d clear often. That also feel valuable to our customers?’

I needed to control the sale during the trial, the same way I’d controlled it everywhere else.

The first place I turned was our analytics dashboard. If ARR was our number one company metric, introductions were a close second.

Quick refresher for newer readers: Whitetruffle was a tech talent sourcing platform. We called ourselves a “dating site for tech talent.” Our algorithm matched software engineers, product managers, UI/UX folks and designers with companies looking to hire them. Employers, our paying customers, would get daily matches. Any match they said “Yes” to triggered a message to the candidate: “Yelp is interested in chatting with you. Want to get connected?” If the candidate said “Yes,” an introduction was made through the platform.

Classic double opt-in. And introductions were critical, because they were the leading indicator of marketplace liquidity. The more intros we delivered, the more value both sides were getting.

I dug in and looked at how many intros our trial customers were getting on average during the 14-day window. The number was 4 to 5.

So on the Account Optimization Call, I started telling new trial customers something specific:

“You can expect to get 2-3 intros during your fourteen-day free trial with us.”

Narrative for success: set.

From that moment on, about 60% of our trials converted to paid. Perhaps the part of the funnel I was most proud of.

Why it worked

Three things were doing the work. And these three components are what you could try to recreate for your own product.

The first? The narrative was anchored to an objective metric tied to value derivation from our product. There’s no arguing with a metric. As a matter of fact, when trial customers would reach out mid-trial complaining about their lack of intros, I’d pull up their account. If they were doing well objectively, I’d respond, “You guys are seven days into your trial and already have 3 intros. That’s a lot more than most. You’ve gotten the number of intros we’d expect for the entire trial! Candidates are responding very well to you guys. You’re a sexy company.” That helpful reframe would most often get the trial customer to calm down and rethink how they’d initially perceived their experience.

The second: prospects were conditioned, pre-trial, to expect those “aha” moments of value. Just like Pavlov’s dog. They walked into the trial knowing the intros were the event to watch for. So when one landed, the thought was, “I’m getting to meet with a candidate I was interested in. This is awesome. I wouldn’t have been able to do that were it not for Whitetruffle.” The value got attributed to the product. And it didn’t happen by accident. We had planted the seed.

The third: we deflated the number artificially. The real average was 4 to 5 intros for a 14-day trial. We told them to expect 2 to 3. I wasn’t sandbagging for the sake of it. I was making sure we cleared our own bar more often than not. We turned the trial outcome into a layup rather than a three-pointer. And nobody was disappointed. Because the customer was still getting three distinct moments of value.

Engineering your own version

Let’s face it. My Whitetruffle story only goes so far. It’s got some compelling pieces. A pattern you might be able to see and appreciate. And even use. But you’re going to have to build out your own version. So let’s get to the takeaways you might want to apply to your startup.

Start with the anchor metric. This is the foundation. Get it wrong and nothing else matters. A good anchor metric has three properties. It’s objective, so there’s no debating it. It’s tied to value derivation, meaning it represents your product doing the thing the customer hired it to do — not engagement, not activity, but outcome. And it fires inside the trial window, often enough to be felt. If your value moment only shows up at day 45 and your trial is 14 days long, you have a different problem to solve before you ever get to the Success Narrative.

What disqualifies a metric? Anything the customer has to self-report. Anything lagging. Anything that lands too late in the trial to matter. Anything they have to interpret subjectively to even know it happened. Logins don’t count. Neither do dashboard views. “They seem to like it” doesn’t qualify.

For a marketplace like Whitetruffle, the metric was introductions. For a horizontal workflow tool, it might be the number of core workflow actions completed by some number of teammates. For a vertical SaaS, it could be something like the number of domain-specific transactions processed end-to-end. For a PLG bottoms-up product, it might well be the number of teammates invited and active. The pattern is consistent: the metric represents the product doing its job.

Then comes the conditioning. The metric does its job if the customer is looking for it when it happens. Otherwise the aha moment fires and they don’t even notice. We conditioned our trial users on the Account Optimization Call. By the time the prospect hung up, they knew intros were the thing to watch for. They knew why intros mattered. They knew what one would look like when it landed. So when it did, the value got attributed to the product, not to luck or timing or some other vendor they were also testing. If you don’t have an onboarding call, the conditioning has to happen somewhere — your activation email sequence, your in-app welcome, your kickoff doc. The channel matters less than the fact that someone, somewhere, is telling the customer what to look for, why it matters, and what it’ll look like when it shows up.

Finally, we’ve got the deflation. Take your honest average and shave a meaningful chunk off the public number. Whitetruffle was at 4 to 5; we said 2 to 3. If your data is noisy or your sample is small, shave more. You can always over-deliver. You can rarely walk back a miss. And remember why you’re doing this: not to lowball the customer’s experience, but to make sure the trust-building moment lands. Trust converts. Stretch goals that miss do not.

Where this falls apart

A few failure modes I see all the time.

The metric is too lagging. Founders pick something that technically represents value but doesn’t fire until the trial is nearly over. Customer hits day 12, hasn’t seen it yet, panics, churns. The fix: pick a metric that fires early and often, even if each unit of value feels smaller.

The conditioning never happens. The metric exists. The customer hits it. And they don’t notice. Because no one told them to look. The “aha” moment evaporates without leaving a fingerprint. The fix: build the conditioning step in like you’d build a feature. It’s not considered optional.

The number gets picked by vibes. Someone in a meeting suggests a round number that sounds good. It has no relationship to actual customer behavior. Half your trials miss it. The fix: pull the data first. Always. If you don’t have the data yet, run a few trials with no public number and watch carefully before you set one.

And the worst failure mode of all: no narrative at all. Just hope. “We’ll see how they get on with the product.” That’s not a sales process. That’s wishful thinking.

Pulling it together

When you’ve got the three components in place — anchor metric, pre-trial conditioning, deflated target — something quiet but powerful happens. You stop running around trying to satisfy a variety of customer expectations. You’re now running one play. For everyone.

That’s what makes it engineerable. And it’s teachable to the next salesperson you hire. That’s what makes it scale.

If you want me to take a look at the Success Narrative you’re crafting for your own product, you know where to find me: paul@gassee.com.

We’re done for this week. We’ve now covered Driving the Success Narrative during a pilot or free trial. A critical component if you want folks to convert from testing your product to being outright buyers. Our next installment will be dedicated to the proposal review call. A good proposal review can help you close a lot of deals. As opposed to dropping the ball at the most crucial time: right when you’re at the goal line. See you soon.

“I can’t believe I haven’t heard back from them. They loved our product when we demo’d it to them. They couldn’t wait to get their hands on it, they told me. Why am I having to follow up for the fourth time? This is driving me crazy!”

I hear the above a lot. The demo crushed. The prospect told us they’d circle back with their team to figure out when to schedule the next call. And then…silence.

The deal didn’t die because the product was wrong. Or the pricing was off. It died in the white space between two stages of your sales process.

Over the past decade, hundreds of founders and startup operators have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the series unfolding in the coming weeks, we’ll cover the essentials needed for a sturdy sales process, and the factors to consider when you go about designing it. You’ll walk away with the necessary tools to start engineering your process from scratch, and the things to look out for as you take it to market for refinement. So sit tight. Tune in. And, as always, be loud with your questions. Here’s your third installment.

Last time, we laid out the Lego blocks. The non-negotiables. The components every B2B sales process needs in some shape or form.

This week is about the synapse between steps in your sales process. And how to cross it to connect the stages together so the whole thing holds together.

Because here’s the thing: you can have every component right and still lose deals. Constantly. You’ll watch qualified prospects evaporate between stages. Meeting show-up rates that look like an empty restaurant on a Tuesday night. Agreements that sit in inboxes for weeks. And you wonder why your beautifully crafted process isn’t producing closed deals.

The answer is often the same: the connective tissue is weak. Or missing altogether.

So, let’s talk about it.

Selling the Next Step

If you’ve ever talked to me about sales for any length of time, you’ve heard me preach on this topic. Selling the next step is the bridge between the stages of your sales process. And this bridge has to be value-laden. Heavy with reasons the prospect needs to show up to whatever comes next.

Not, “Hey, can we get something on the calendar for next week?”

That’s not selling the next step. That’s begging for it. And it gets you exactly what pleading gets you in sales: maybe a meeting, perhaps a no-show, definitely no momentum.

Selling the next step means making the next meeting feel like must-see TV. The prospect should walk away from the conversation thinking, “I’d be an idiot not to show up to that.” Anything less, and you’re rolling the dice on whether they prioritize you over the seventeen other things screaming for their attention.

Let me tell you how I learned this lesson the hard way.

Enter Fitz

Back at Whitetruffle, the first sales hire I made was a guy named Chris “Fitz” Fitzgerald. I knew I’d recruited the right person within his first few days with us. Fitz handed me a book with a bright red cover, as he got to our sales desk one morning. “You’ve got to read this”, he said.

The book was The Challenger Sale. I devoured it over a long weekend. I now gift it to every new client that signs up for our coaching.

Fitz was a student of the game.

At this point, I had already built out our sales process from scratch. I had a playbook documented. We also had a go-to-market motion that overwhelmed me with sales calls. It’s why we hired Fitz in the first place. Part of his onboarding was handing him the playbook. Walking him through every stage, every script. And making sure he was set up to succeed.

A few weeks in, I noticed something.

Fitz had a no-show problem at our Account Optimization Call.

As context: the Account Optimization Call was a fancy name for our trial onboarding call. At Whitetruffle, we sold through a 14-day credit-card-activated free trial. The qualification call came first: a 15-minute conversation where I’d get prospects excited about the service and qualify them fully. From there, the Account Optimization Call was the forcing function that got them on our trial.

I’ll get to why that call came to exist in a second. But back to Fitz.

His no-show rate was hovering above 50%. Half of his qualified prospects were ghosting the very next meeting. We weren’t recording Zoom calls back then like we do today. We were taking sales calls over our iPhones. But Fitz and I shared an office. So I started listening to the back end of his qualification calls. Particularly the part where he was selling the Account Optimization Call.

Two things stuck out:

One. He lacked assertiveness.

Two. He wasn’t laying out the value of the next call clearly enough.

The prospect was asked to give up another 30 minutes. And they couldn’t fully see why it mattered to them. Why they’d benefit from attending.

So I asked Fitz to memorize the script. Cold. My favorite way of doing this — and one I recommend to every client — is to have them repeat the script out loud in front of a mirror. Five to ten times a night before bed. Within a week to ten days, the script is fully internalized. And once you’re not fighting to remember the words, you can deliver them with aplomb.

Within a week or so, Fitz’s show rate went from sub-50% to 90%+. The industry standard you should benchmark against for any sales meeting that’s been booked.

His funnel was fixed. He started hitting quota. And he became a strong contributor to our sales team.

The whole episode was a stark lesson for me in just how much downstream damage a poorly-sold next step can cause.

Selling the next step is one example of a much larger principle: controlling the sale.

Losing control of the sale happens to the best of us. It’s interpersonal by nature, so it’s never fully controllable. But every degree of control you give up is variability you’re injecting into your sales process. And variance is the enemy of repeatability.

I learned this one the hard way too. Long before I hired Fitz.

Flash back to early Whitetruffle. I was tasked with building out our sales motion from scratch. I went to one of our silent cofounders, Mike Morrell — a mover and shaker in The Valley — for advice. Mike’s read? Perhaps we didn’t need a demo given our price point and the deal velocity we were seeking. “We might not need a full enterprise motion,” I remember him saying.

So I kept it simple. A 15-minute discovery call to get folks excited and fully qualified. At the end, I’d say something like, “Great, what we’ll do is send you a link to sign up for the 14-day credit-card-activated free trial. We’ll be monitoring your account during the trial, and we’ll reach out if we need to course correct. If you’re satisfied at the end of the 14 days, you’ll convert into a paying customer. You can of course cancel anytime during the trial.”

Sounded clean. Felt right. Should’ve worked.

Guess what actually happened?

Two-thirds of fully qualified, excited prospects never signed up for the trial.

For weeks, I was beside myself. Banging my head against the walls of our sales lab. These were folks who had told me, on the call, that they needed to hire engineers. That they had open reqs. That they wanted to get started. And yet most of them were vanishing the moment the link hit their inbox.

That’s when I had to accept one of the harder truths about human nature in sales: people don’t do what they’re supposed to do.

Even when it’s in their best interest. When they’re excited. Or when they told you, twelve minutes ago, they would.

It becomes our job to herd the cats. To tighten the screws. To control every variable we possibly can. Because anything we leave to chance is something the market might gleefully steer away from us.

As a last ditch attempt to stop the bleeding on my hemorrhaging funnel, I instituted the Account Optimization Call. The same one Fitz would later have to learn to sell properly. The pitch was: this is a 30-minute call where we walk you through the product in your own trial instance and set you up for success for the first 14 days and beyond. You hold onto the wheel. We guide you through the product in real-time. And by the time we’re done, you’re fully briefed on every bell and whistle of the service.

It worked. Overnight, fully qualified prospects were now showing up to our scheduled Account Optimization Call.

Here’s the kicker. About a third of the people who showed up to that Account Optimization Call hadn’t yet started their trial. Their credit card information hadn’t been entered. So I’d say, “No problem at all. We’ve got 30 minutes. More than enough time to walk you through the product. Why don’t you grab your CFO’s credit card. Or use your own business card if you’d prefer. Sign up for the free trial right now and we’ll get you set up.”

Our funnel was instantly fixed. We had just found a way to control the sale.

Selling the next step and forcing functions like the Account Optimization Call are just two of several things you can institute to control the sale. Let’s run through some others.

Recruit all stakeholders to the group product demo. Assuming you obtained the buyer journey during discovery (and you did, right?), you know who the stakeholders are. You know who’s going to weigh in on the decision. Who controls the purse strings. Now, you’ve got to get them in the room for the product demo. Each stakeholder has different pain points. Different concerns. Different reasons that might block or champion the deal. The demo is your shot to address all of them at once. Don’t waste it by demoing to your champion alone and hoping they’ll relay your message faithfully. Make sure you can expose all of your stakeholders to your product’s value.

Book the onboarding call before the agreement is signed. This one is where I see folks consistently leave money on the table. You get the verbal close at the proposal review. Prospect’s agreed to move forward. Junior rep’s instinct? Send the agreement. Wait for the signature. Then book the onboarding call.

No bueno.

Book the onboarding call, as a kind of double close, and then send out the agreement for signature. Make the onboarding call the forcing function for the signature. “Great, I’ll send the agreement over today. Let’s get the onboarding call on the calendar for next Tuesday so we can hit the ground running. We just need the contract executed before then so our implementation team can prep and take care of you guys from here on out. Can we make that happen?” You’re obtaining a commitment from your prospect that the signature will be done by the time you meet next. Without it, agreements sit in inboxes. And time, as you’ve heard salespeople say since the dinosaurs roamed the earth, kills all deals.

Arm your champion when you can’t get in the room. I don’t love having someone else sell on our behalf. But sometimes you can’t get the CEO, the CFO, the big boss in front of you, no matter what you do. When that’s the case, you arm your champion with everything they might need to represent us well. ROI calculator they can run their boss through. Marketing collateral tailored to the decision maker’s concerns. A one-pager addressing the specific objection you know is coming. Whatever you’ve learned about the decision-maker during discovery, build the ammo to match. Your champion is going to walk into someone’s office and try to do your job for you. The least you can do is give them a fighting chance.

Drive the success narrative during a pilot or free trial. This one deserves its own episode — and it’s getting one next. For now, just know this: if you’ve got a prospect in a paid pilot or a free trial, you can’t afford to let them define success for themselves. You drive that narrative. More on that in our next installment.

That’s enough for this week. We covered the connective tissue between the steps of your sales process — selling the next step — and the broader discipline it’s a part of: controlling the sale. As mentioned above, next episode, we’ll zoom in on something that determines whether your pilots and free trials ever convert into paid contracts: driving the success narrative. Most founders assume the product will speak for itself during a trial. And yet, the customer comes to a verdict. And if you’re not the one shaping it, someone or something else will. We’ll get into how you can provide expectations. All while talking about one of my favorite topics: restaurants. See you soon.

“Well we don’t have much of a process right now. But you have to realize that we’re just getting started. I’ll qualify our prospect on the first call. And then book a full product demo. And if they’re excited about what we just showed them, I’ll send over a POC agreement for signature. I’ll then schedule a followup call, so we can discuss how the pilot will run. But a lot of the prospects we’ve spoken to haven’t been biting on the POC despite the fact that it’s free. I just don’t get it.”

This is an excerpt from a consultation session I just had with a potential new client. And I can’t say it’s the exception. Regularly, I’ll meet with founders that are just taking their products to market. But don’t have a set process for their sales conversations.

Over the past decade, hundreds of founders and startup operators have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the series unfolding in the coming weeks, we’ll cover the essentials needed for a sturdy sales process, and the factors to consider when you go about designing it. You’ll walk away with the necessary tools to start engineering your process from scratch, and the things to look out for as you take it to market for refinement. So sit tight. Tune in. And, as always, be loud with your questions. Here’s your second installment.

The result?

I’ll lay it out for my clients, “It’s almost impossible to lead your prospect through a sales conversation, if you don’t even know where you’re headed. You need to be the sherpa. Your prospect’s guide throughout. If you don’t have a plan on how to get from base camp to the summit, it’s going to be very difficult for you to convince others to follow you. I can assure you that.”

I’d much rather you have a rudimentary sales process that’s far from perfect than nothing at all. You’re much better off designing a way to close customers that you end up refining over time – based on market interactions – than no path to revenue.

Last week we covered the major pitfalls you should steer clear of when conducting your sales process. But now it’s time to actually lay out the components you’ll need to include to be successful in startup B2B sales.

From avoidance. To inclusion.

And what we’ll be going over are absolute must-haves as you design and engineer the sales process for your startup. Miss on any of them and you’ll find yourself quickly in deep waters. With strong currents. Desperately trying to swim back to shore.

So without further delay, here are the non-negotiables for your sales process in business-to-business sales. Even if you’re just starting out.

Qualification is the art of making sure you’re not wasting time with leads that don’t have a chance of closing in short order. A salesperson’s most precious resource is their time. We want to focus our time, energy, and resources on deals that have a chance of closing in the near future. That means vetting for all of our ICP criteria, including timing/urgency and budget. If you miss on qualifying your prospect tightly, you’ll end up chasing prospects like a jaguar chasing the fastest antelope on the African plain. You go hungry. And question your hunting abilities. Had you fully vetted your prospect, dinner would have been served with greater ease than pressing the “Place order” button on the DoorDash mobile app.

Conducting Discovery is about doing two things. One: unearthing use cases you can tailor your demo around to make it more appealing to your prospect. And therefore far more impactful. Two: and even more importantly – we aim to get our prospects to confess their pain to us – and to themselves. That’s more than half the battle in sales. Because the only thing we have to do is map the product to being the painkiller. Our prospect then can’t help themselves from wrestling the product out of our hands. Omit this part of the exercise, however, and it becomes virtually impossible to close any deals. Nor instill any urgency. Prospects have a hard time understanding how you’ll solve their most pressing problems. And you end up producing demos that feel generic and bland. Yuck.

Obtaining the Buyer Journey is about making sure you know the terrain you’re going to traverse to not only get a deal done, but also to implement our product at our customer’s. A sales process doesn’t end at signature. It ends at our customer deriving value from our product. We want to obtain the steps, timeframes and stakeholders we’ll need to go through in our buyer’s journey. The question I like to start with: “How do you typically buy a solution like ours?” Fail to get a detailed answer and you run the risk of getting your deal derailed. If not, kill it outright.

The most simple example of this? You get your champion Ted very excited about your piece of software. You didn’t bother to obtain the buyer journey and thus didn’t know that their boss was to be involved in the decision-making process. Your champion walks into their boss’ Peter’s office and exclaims, “I met with Jake over at Acme Corp. They have an awesome AI product that could make our lives so much easier…” Within half a second, Peter steps in, “Ted, how many times have I told you we’re not spending any more money on AI products for the rest of the year. We’ve been burned before and are all set for now. Please quit spending your precious time on calls with vendors!” Ted, dejected, walks out of Peter’s office. Fully realizing his lack of political capital within the organization. You follow up diligently over email. 7 times. But never hear back. Ted is too ashamed to admit he’s got no juice. Plus, he’s been given strict orders. Your deal got ambushed by a stakeholder you should have known about.

The Product Demo is usually considered the piece de resistance by most founders. It’s a critical time for you to showcase your product to your prospect. The more tailored you can make it – with the prospect’s own use cases, documents, or data – the better off you’ll be. And remember: nobody wants to buy yet another piece of software. So, make sure to tie each feature, module or functionality back to value for your customer. There’s a simple question you can ask yourself at the end of every user flow, feature or functionality you showcase. “So What?” is a blunt inquiry into whether or not you made a good enough case as to why your prospect should care. Use it as often as you can. And you’ll get better at reminding yourself that just because a feature is “cool” doesn’t mean you’ve articulated its inherent value to your customer. If your demo doesn’t end up being impactful, customers will politely bow out of having further meetings with you, or deprioritize the initiative altogether. You’ll go from having them sitting on the edge of their seats anxiously awaiting to see your product, to them searching for other ways to solve their problem.

We’re getting to the business end of your process. You’re going to have to present commercials and pricing to your prospect. Just so they can be informed on the decision they’ll make when purchasing your product. It’s also a time where you’re going to want to surface and handle objections, if they exist. Only to then obtain the verbal close. This step is all about constructing your offering in a compelling way. Making sure the terms are palatable to both parties. But also having the wherewithal to dig for the roadblocks preventing us from moving forward. And finding creative ways to get around them. Botch this component of your process, and your prospects will run for the hills. You’ll be left wondering why you spent so much time with them, only to come out of the interaction empty-handed.

Lastly, your onboarding or kickoff call is not only the start of you implementing the product at your customer’s. But it’s also a good forcing function towards getting your prospect to sign the contract and maybe even make the first payment. It bookends your sales process. Without it, you’re not ensuring your prospect is deriving value from your product. And you’re praying the agreement you sent out gets executed quickly. But you could be waiting on your customer for weeks on end.

Having each of these components will not guarantee repeatability. Nor will it ensure you close every deal. But not having each of them in your B2B sales process will only put you in a world of hurt. Consider them necessary but not sufficient conditions for your startup sales success.

Okay we’re done for this week. We went over the essential Lego blocks for any business to business sales process. The next episode in this series will start with us covering the best way to connect them. So as to ensure that folks stay on the tracks towards closing. We’ll learn about the crucial nature of building such a bridge. And how to go about assembling that connective tissue. Ciao for now.

“I just demo our product. And then I’ll send out a quote with a payment link. A lot of customers will ghost us after that. I can’t quite understand why because a lot of them seemed excited about what we had built.”

I’ll hear this narrative – or some form of it – from founders that have taken the time, brainpower and know-how to build a polished product.

And yet approach building a sales process with a sheer lack of sophistication.

Over the past decade, hundreds of founders and startup operators have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the series unfolding in the coming weeks, we'll cover the essentials needed for a sturdy sales process, and the factors to consider when you go about designing it. You’ll walk away with the necessary tools to start engineering your process from scratch, and the things to look out for as you take it to market for refinement. So sit tight. Tune in. And, as always, be loud with your questions. Here’s your first installment.

You might be reading the title of this series and wondering, ‘Why the heck does my sales need design and engineering? Isn’t that exclusively the province of my product?’

The answer is a resounding, “No!”

As a matter of fact, if you’re thinking of your startup’s sales that way, you’re missing a large chunk of what you should be considering. Why should you care?

Let me spell it out.

The way you design and engineer your sales process dictates the experience your customer has on their way to buying your product or service. And getting it implemented. The experience they have with you dictates your likelihood of closing them – your close rate – but also sales cycle length, pipeline quality, and average deal size. Sales processes aren’t designed just to increase close rates. They’re designed to make closing deals systematic instead of accidental.

Repeatability is key.

Without it, you can’t even start thinking about hiring reps. And without building out a sales team, all you have is an unpredictable founder-led sales motion. Perhaps a nice lifestyle business. At best.

But nothing close to a venture-scale company. Never mind a unicorn.

That’s why it’s critical to design and engineer your sales process conscientiously. Based on market iterations. Feedback the market is gracious enough to give you.

Before we start diving into the actual build of a process, let’s look at the cardinal sins I’ve observed founders and startup operators make when it comes to their sales conversations. Just being aware of these will help you avoid them altogether. And that should be put ahead of the greater majority of startup founders.

First on the list: sending out blind proposals. ‘What does this actually mean?’, you might think to yourself, if you haven’t encountered the concept before. Well, sending out a blind proposal would have you send a quote to your prospect via email, for example, without taking the time to review the proposal in a meeting with said prospect. Now, why would that be a terrible idea?

In most cases, prospects take a proposal they’ve received, flip to the last page – where the pricing is listed – and make a snap decision on whether or not they can afford it. They might say to themselves, ‘Man, this is far outside our budget. There’s no need for me to talk with Paul anymore.’ I’ll follow up several times over email. And all I’ll get is tumbleweeds. No reply ever again. Nor an understanding as to why the prospect didn’t buy. Which is crucial at the early stages of building sales at a startup. I tell my clients all the time, “I’m not going to hammer you for losing out on deals very early on. But it is a crime not to learn from the L’s we’re taking.”

Now, imagine for a second that instead of sending out the proposal in advance, we had scheduled a call to go over it with our prospect. We can now make sure to defend the value of our proposal. We’re able to detect whether or not that value lands with our prospect. Our floor for this meeting is understanding why our prospect doesn’t buy. Which is critical. Our ceiling for this proposal review meeting includes us getting an opportunity to surface and handle objections. Pull out discounts or other things from our back pockets, if need be. And obtain the verbal close. As you can tell; a much different outcome from getting ghosted without knowing why the person didn’t buy. Thus the importance of always booking a meeting to go over the proposal with your prospect. All the while making sure you don’t send the proposal in advance of that meeting.

Our second sin? Not qualifying properly. Let’s take a quick step back, for the uninitiated. Why do we even qualify in sales? Because our most precious resource as salespeople – and I’d even venture to say as humans – is our time. And we don’t want to waste time on deals that have very little chance of closing in short order. So we qualify for all of the qualification criteria in our ICP. In addition to things like timing/urgency, budget. What happens when you don’t qualify well? You let prospects through and into your sales pipeline that have no business being there. Which has you wasting time chasing deals that shouldn’t be opportunities. And sinks your close rates. As a matter of what, when clients come to me – complaining about their close rates – the first place I look is their qualification process. You want to qualify your prospects as early as possible in your sales process. Preferably in the first meeting you have with them. And make sure you’re not loose with it. Do that, and you’ll save yourself a ton of time and headaches later on.

Our third sales process sin to avoid at all costs? Giving pricing too early. Now, why would that be harmful to us? And our chances of closing? Quite a few people will call salespeople “manipulative” for holding off on giving pricing too early. And it could well be an accurate descriptor. But there’s a legitimate reason why salespeople don’t give pricing too early. At the very beginning of your sales process is when the perceived value of your product in your prospect’s mind is at its lowest. We’re talking about complex products with a high price point, here. Not strawberry lollipops you sell for fifty cents each.

In the very early stages of any sales process, you haven’t had the opportunity to convey much if any value. And you haven’t built any trust. You’re just about to start talking with your prospect directly. Over time, you are there as a salesperson to increase that perceived value in your prospect’s mind. So, if you go about delivering your pricing right off the bat, there’s a great chance your prospect hasn’t fully groked your product’s value. Which will mean they might experience sticker shock and opt out of further interacting with you.

If, on the other hand, you give yourself the time to build up the value in your prospect’s mind through several conversations and also develop trust over that time span – before unveiling your pricing – there’s a much greater chance your prospect thinks to themselves, “Wow, I’m going to make a 12X ROI on this product. I might just have to buy it.” The sticker shock response gets eliminated and you’ve given yourself a much greater shot at the sale. Remember that next time you’re tempted to give pricing early on. Even if your prospect asks for it.

The last two sins I’ll allow myself to group together. Because they’re highly related. Shame is a destructive emotion. One of the worst we can experience as humans. But I’ll often joke with my clients that I’ll allow them to hang their head in shame if they leave a sales meeting without booking the next conversation. It’s Sales 101. Why is that considered crucial?

Without booking the next conversation, you run the risk of having folks fall through the cracks. They might not reply to your followup email and never book another conversation with you. Or that they take a while to respond. And knowing that time kills all deals, other things might pop up and divert their attention away from doing business with you. And you’ll be fighting to find ways to get them back into your sales funnel and onto the tracks towards closing. Including asking yourself a recurring question, ‘What value can I dangle to get them back on a call with me?’ Not an ideal situation to say the least. How much better would it feel to have the next conversation booked in the calendar, properly sold to your prospect as valuable to them with all the required momentum to seal the deal?

Selling the next step – whose omission is our last cardinal sin – enables you to accomplish all of that and make sure your prospect shows up to the next meeting. More on that in a subsequent episode in this series.

Okay, that’s enough for this week. I wanted to make sure you knew why sales process design and engineering was crucial to your success in startup sales, and what pitfalls to avoid. Next week, we’ll start looking at sales process non-negotiables. Items that all B2B sales processes possess in one shape or form. Forget to include any one of them, and your revenue generation is likely to implode. See you for the next installment.

“Paul, cold email never works on me. I don’t think we should try it here.”

“I don’t feel comfortable reaching out to folks in this manner. It just doesn’t feel natural to me.”

“We’re going to go back to building product. Once it’s perfect, it will just sell itself.”

Just some of the concerning statements I’ll hear from founders in session, as we think through their go-to-market strategy.

Over the past decade, hundreds of founders and startup operators have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the series unfolding in the coming weeks, you will not get only the required frameworks to get you thinking properly about prospecting as a founder. But you’ll get the tools necessary to generate consistent pipeline for your company. So sit tight. Tune in. And, as always, be loud with your questions. Here’s your seventh and final installment.

Last week was about designing and ranking experiments. Their importance in answering the questions you have for the market. Questions elicit experiments. And the experiments garner answers. In go-to-market, the earlier we get to a successful experiment, the better off we are. Because, we can scale it, and start generating sales conversations in a repeatable way. Thus our reason for ranking the designed experiments based on their likelihood of success.

This week, let’s get into the disposition you should have as a founder when it comes to your go-to-market. Mentality that – as you’ll see – is far from the pronouncements made above.

The most successful founders are those that are looking to learn from the market as much and as quickly as possible. Those who remain humble and agnostic as to what might work. They may have strong opinions about what experiments might be successful but they’re more than happy to put them to the test, and even relish in being proven wrong. They lean into the market relentlessly.

Ever see how a surfer relates to the ocean? The surfer reveres the water he floats on. And rightfully so. The ocean is a much greater force than the human riding its waves. I invite my clients to see the market in very much the same way. Even if we end up growing our startup to become a Fortune 100 company, the market will still be a much more powerful force than we will ever be. We therefore need to treat it with the utmost respect. Bow to the market, and learn how to listen to it. After all, it holds the truth. Our job? To interact with it, listen to it carefully, and iterate on our go-to-market approach based on what it’s telling us. Perhaps the most important skill I teach my clients over time is this ability to read the data and feedback coming from the market. It all starts with a strong dose of humility, and a reverence for the market.

You might now ask me, “Well, Paul, that’s all well and good. I already think the world of the market, and what it has to teach me. But what does listening to the market look like in practical terms?”

Great question. Qualitatively, here’s an example to illustrate what I mean. You get a “please remove me from your list” reply from a prospect that you had sent an automated email to. What does one do with that? Well, you need to go find out why you got that response, by humbly asking your prospect for feedback. Once in a while, you’ll land on a golden nugget. One that ends up completely transforming the way you go-to-market.

“The pain point you mentioned in your email isn’t something we deal with a lot. It didn’t feel worthwhile to continue the conversation”, your prospect replies.

Yes, this is a small sample size. N of 1. But one reply might have you realize that you ought to be leaning on another pain point as your entrée into a sales conversation. Next thing you know, you’re deploying a different pain point in your email campaigns and they take off.

How does listening to the market look like quantitatively?

Glad you asked. A 4-step 100-lead automated email campaign gets fully deployed and the data is in: a 60% open rate and a reply rate of 3% with no interested replies. Now, what does that all mean? Our emails are getting delivered in inboxes and our subject lines are strong enough that folks are opening them. The missing ingredient is email body copy that’s more engaging. Our emails are presumably getting read at a good enough clip. What’s missing is copy that gets people to reply. And respond to us with interest. We ought to take a closer look at the offer/CTA we’ve put forth. Can we make it more value-laden and immediately attractive to our prospects? Can we dangle value so irresistible prospects have no choice but to book a call with us?

This is a glimpse as to what you need to get to when it comes to listening to the market. I’ll allow myself a detour to not only show you how sophisticated you need to become in that realm, but also to perhaps challenge the way you’ve been thinking about go-to-market overall.

A few years back, a European software vendor approached us with a problem. Despite having 13 or 14 big brands as customers – companies anybody that has been involved in business for even a couple of years would recognize – they were having a hard time generating consistent pipeline. And they wanted to do so through an automated email initiative. I was amazed they were struggling with their top-of-funnel with such big name customers as social proof. Their ACVs were $60K. I got this startup’s CEO to agree to giving our engagement at least 4 months. This – all while knowing – that it can sometimes take upwards of 12 months to find message-market fit. We set forth on building out this initiative. And launched it.

See the report below from this outbound buildout. Do know that we never share client data unless it’s been completely scrubbed and anonymized. Which this has.

A few things to note about this anonymized report. First, each row is a different campaign that was launched. Second, the taxonomy of each campaign name works as follows. It starts with target vertical. Then goes to launch date. Only to finish with copy variation. Also, every teal-highlighted row is one that has reached the 1% interested rate plateau or above.

Now, check out what happens with this automated email initiative. After launch, we don’t get our first interested reply till our fourth campaign. Then we go ambling into the desert without much to drink for a while. We only get a gulp of water – our 2nd interested reply in our 19th campaign. Then nothing till our 31st campaign; where we got our 3rd interested reply. And then nothing till our 40th campaign – where we get our 4th interested reply. 40 campaigns. Only 4 interested replies! Tough sledding, right?

Look at what happens next, however. Teal starts appearing quite a bit more. So much so that about two, two and half months in, in the span of 5 campaigns – three of which are at 400 leads, we generated 18 interested replies. And four and a half, close to five months later, we generated 36 interested replies in the span of 6 campaigns. All at 400 leads. At this point, we’re getting to message-market fit. We’re generating hundreds of thousands of dollars worth of pipeline on a weekly basis. This report gets cut off below for our purposes. But it kept going. We worked with this company for over 18 months. Close to 2 years. They ended up integrating our process, bringing it in-house. Needless to say, they were thrilled with us.

I’m showing you this report for two reasons. The first? If we were to inject this startup’s CEO with truth serum today and ask him, “Were you thinking about pulling the plug on this initiative two, two and half months in?” I’d bet you he’d say, “Yes!” I could hear his impatience and anxiety in our weekly calls with him early on in the outbound buildout. The other reason? When I meet with founders and startup operators, I’ll sometimes ask them if they’ve tried automated email, among other go-to-market channels. And they’ll respond, “Yes, but it didn’t work.” I’ll then ask, “How many campaigns did you launch?” “Eight campaigns and we only got a couple replies.” My usual response? “I don’t think you quite understand what it takes to find message-market fit.” The report above shows an arduous journey to message-market fit. A lot of times, we don’t feel like we’re getting enough dopamine to keep going. Hopefully this document shows folks that it’s possible to get there if you have enough persistence, know how to write good outbound copy, listen to the market well, and possess advanced data analysis skills. Now, we’ve seen and worked with startups that get a lot more teal earlier in the process. But it’s important to note that this report exemplifies what it can take to get to message-market fit. And if folks give up too early on this — or other — channels, they run the risk of never giving their product a chance to see the light of day.

Having seen all of this, how has your understanding of go-to-market changed? And how sophisticated do you think you are in this realm?

I ask because a lack of sophistication in go-to-market could be the difference between finding a repeatable way to get in front of customers, and not having your product ever get a chance to move off your shelves. Which group do you want to be in?

If it’s the latter, I’d encourage you to find the help you need to get this know-how and sophistication as quickly as possible. As you can probably now tell, prospecting takes a lot more sophistication than you had imagined.

Then why go at it alone?

Getting a good coach that knows the ropes can help you accelerate your learning and make sure you adopt the right disposition to tackle your market. I’m here as always if you want to chat. For anybody that writes in, in response to this episode, I’ll happily offer a free hour-long coaching session. You bring your top thorny sales and GTM issues, and my job is to help you through at least one of them. As always, take these learnings, use them out in the market and report back. I’m eager to see what sticks with folks and what ends up working for them. Chat with you soon, hopefully.

This was the final episode of the Founder-Led Prospecting series. Hope it was useful. If you’re landing on this installment first and would like to start where it all began, here’s our first episode. Remember: prospecting is far from glamorous but oh so essential to your sales. And thus your startup. Give it proper attention, and you’ve got a shot at surviving. Ignore it or bury your head in the sand, and you’re more than likely headed to the startup cemetery.

Last time, we made sure to discuss the importance of metrics, and their role in startup sales and go-to-market. Now that we have these metrics, you might ask, “Where do we even start, Paul? How should we think about building out a sturdy top-of-funnel? It’s all fine having a North Star to aim at, but how do I effectively establish my go-to-market?”

Over the past decade, hundreds of founders and startup operators have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the series unfolding in the coming weeks, you will not get only the required frameworks to get you thinking properly about prospecting as a founder. But you’ll get the tools necessary to generate consistent pipeline for your company. So sit tight. Tune in. And, as always, be loud with your questions. Here’s your sixth installment.

Startups are experiment machines. Anyone that doesn’t recognize this puts their venture at risk. What you want to do is to learn about the world around you as quickly as possible. Once you’ve received funding, you’re sitting on a ticking time bomb. The faster you learn about reality, the better shot you have of building a product folks want. And moving it off your shelves and into customers’ hands. All before your runway runs out.

How does one do that?

You start by asking the right questions. The meta inquiry I like to use to elicit all the questions I might have about reality: ‘What would I like to learn about the market?’

When they first started, Netflix’s founders might have asked themselves, ‘Are consumers willing to wait for DVDs in the mail, versus getting them immediately at a retail location?’ Or Brian Chesky, founder of Airbnb, might have pondered, ‘Will hosts post photos online to advertise their spaces to travelers?’ Or perhaps Marc Benioff wondered, ‘Are customer-facing teams willing to entrust their data to the cloud?’ I wasn’t in the room for any of these inquiries, but I’m sure some version of those questions were posed. And these founders had to either find ways to answer them quickly – through cost-effective, feasible experiments – or break down these inquiries into smaller, more bitesized questions they could then get answered through experiments.

I, myself, had a question I was itching to answer when I was running sales at Whitetruffle. I knew we had two valid ways into the companies we sold to. I was dying to know however, ‘What’s the better entry point into the organization: the technical leader or the recruiter?’

I had to design an experiment that was going to help me get my answer.

Here’s what I came up with:

2 X 100-Lead 4-Step Automated Email Campaigns, 1 targeting Heads of Recruiting & 1 targeting VPEs/CTOs

The results came in 2 weeks later:

Campaign A to Heads of Recruiting: Open Rate: 45%, Reply Rate: 3%, Interested Rate: 0%

Campaign B to VPEs/CTOs: Open Rate: 51%, Reply Rate: 6%, Interested Rate: 1%

This first experiment started to show us that perhaps there’s a better way into the organization through the technical leader. We’re not ready to make a final determination yet, as it’s only one experiment. But it’s solid early signal.

So, what ended up happening at Whitetruffle, as it pertains to our entry point question? Well, after running dozens of experiments like this one, we came to the conclusion that both entry points did work well. But if I had my druthers, I’d pick the technical leader over the recruiter any day. Reply rates were higher, sales cycles were shorter, and deal velocity picked up quickly after the first call. Our explanation for those results?

Well, first and foremost: VPs of Engineering or CTO’s were more likely to feel the pain we were eradicating more directly than recruiters. Whitetruffle helped employers source and meet with technical talent – software engineers, UI/UX folks, designers and product people – based on their open job reqs. If a technical leader was to miss a product deadline, their derrières were on the line. And more often than not, tech team constraints were to blame. An issue we’d help with by enabling them to hire technical employees more quickly. Second, technical leaders possess a lot of political capital within their companies. If they’re not the most important department head, they’re tied for first with the revenue leader. Meaning, when they had chatted with me on an introductory call, and then suggested to Recruiting that they should consider us, things moved fast. Recruiting considered the technical leader their internal client, and they’d scurry to serve them. They’d enthusiastically take the next call with me, and we were off to the races. Lastly, I bet we were able to seduce technical leaders intellectually. As a reminder: we described Whitetruffle as a dating site for tech talent. We matched these technical candidates with employers looking to hire them based on a matching algorithm that looked at 50+ core signals. My educated intuition – based on hundreds of conversations with VPE’s and CTO’s – told me that these technical leaders loved that we solved a human problem with a sophisticated algorithm.

Now that we’ve got an idea about how to design impactful experiments based on the questions we want answered from the market, what else can we do to enhance our chances of success?

Well, for any given question you’re looking to get answered, you’re going to want to rank these experiments based on their likelihood of success.

Imagine having 17 experiments listed out to answer the question: ‘what outbound initiative will get us to message-market fit?’ They’re all conjured up and ready to go. The difference between hitting success in one experiment and getting to message-market fit in Experiment 1 versus Experiment 17 could mean months of runway. The survival of your startup could hinge on the way you’ve ranked your experiments. Most founders unfortunately don’t see it this way. And it ends up killing far too many startups.

The earlier you land on a successful experiment, the better off you’ll be. Because you’ll be able to pull hard on a growth lever. If you had the following two experiments to rank amongst the list of 17 we came up with, how would you go about it?

Target: Recruiters

A. LinkedIn Automated Campaign: 3 Steps, starting with a Connect Request and an accompanying note, and two subsequent messages.

B. Automated Email Campaign: 4 Steps, two full pitches in your E1 and E3, with a breakup email as your E4.

Not having read the copy — but assuming they’re both well-crafted, I’d rank Experiment A ahead of Experiment B.

Why is that? Well, my rationale here is based on experience. And go-to-market expertise. (Both things I help my clients with). I’ve seen this movie hundreds of times. I won’t be able to tell you with certainty what experiment is best. Nobody will. Because each startup is unique. With its own set of circumstances: market, product, team, capabilities, etc. But an educated bet will improve your chances dramatically.

I know for a fact that we can reach recruiters via email. I built an automated email initiative that was responsible for 50%+ of our MRR growth at Whitetruffle. Which targeted recruiters among other personas. But I also know that recruiters spend almost every waking hour on LinkedIn. If I’m going to make a bet on an experiment working, the channel is going to matter a ton. And I’d rather wager on the channel my target persona lives on.

We’ve gotten a sense for how experiments should play a role in our go-to-market. Now, how do we go about making the most of these experiments? And why is listening to the market a crucial skill for us to learn as startup operators? We’ll get into that and more in the final episode of our Founder-Led Prospecting series next week. Till then, take care.

Last week was about producing a delectable meal out of our ingredients. In our case: great outbound copy out of our building blocks. We obtained some techniques, frameworks and instruction. In sticking with our theme – recipes. But now, we turn our attention to what success looks like. Because without that North Star, it’s hard to know up from down. What we should be aiming for. And even how to improve. Success – for us – will come in the form of metrics. Because at the end of the day, it’s hard to improve what you don’t measure.

Over the past decade, hundreds of founders and startup operators have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the series unfolding in the coming weeks, you will not get only the required frameworks to get you thinking properly about prospecting as a founder. But you’ll get the tools necessary to generate consistent pipeline for your company. So sit tight. Tune in. And, as always, be loud with your questions. Here’s your fifth installment.

So what metrics should be measuring, tracking and analyzing? If I could be greedy (as Gordon Gekko once allowed us to be), I’d yell out “all of them”. And while that would be nice and certainly a worthwhile quest, we should start with the essentials. The must-haves. The fundamentals. If we’re going to start with automated email outbound – partly because it’s especially data rich, but also because it’s very scalable – the metrics we should capture and examine are laid out in the slide below.

Now, it’s one thing to have them laid out in front of you. Yet another to fully understand them. What impacts them and how you can have some measure of control over them. Let’s dig in.

Bounce rates are about lead data quality and staying out of spam filters. Years ago, when using Apollo, you had to take your leads out of their system, clean them in a service like Neverbounce before bringing them back into your Apollo account to send out your campaigns. That’s how dirty their lead data was back then. They have made significant strides in cleaning things up in recent years, and their data is now decent. But those were the measures we had to take to prevent our bounce rates from skyrocketing. We now use Amplemarket, which has very good data quality (among other things) and has us worry much less about this issue. A bounce rate of 5% or less is what you should be aiming at for each 4-step campaign that is launched. Anything around 10% should have you ringing the alarm, and have you pulling up your sleeves to fix the crisis immediately.

Open rates are governed by the quality of your subject lines and how good you are about staying out of spam and getting delivered in the main inbox. And you’re going to want to be between 40 to 60% for any 4-step campaign deployed over two weeks or less. If you’re above that range, you’re doing even better. Can you avoid words like “free” in your email body copy – which tends to trigger spam filters? Can you make your subject lines so irresistible prospects can’t help but click on them? Those are just two amongst a sea of questions you should be asking yourself.

Reply rates are all about the engagement garnered by your email body copy. If your emails are getting opened, what are you putting in the email body that gets folks to reply to you. And when I say “reply”, I mean the whole array of replies. From “Please unsubscribe me”, to “here’s my colleague Andrew, who you should chat with”, to “let’s jump on a call next week please”. Any reply is encapsulated in this metric. And we’re aiming to hit 6%.

Interested rate is short for “interested reply rate”. Any replies that indicate interest in your product or service should be tabulated in this metric. (If you want examples of the types of replies that fall under the “interested” category, drop me a line at paul@gassee.com, and I’ll send you a slide containing them). A lot of what is going to dictate an interested reply is your email body copy, but also the call-to-action/offer you put in front of your prospect. We’ve seen this metric jump by getting creative and dangling a lot of value upfront. I’d challenge you to think this way. For this one, you’re going to want to hit 1% as your target. The reaction I get more often: “That’s it, Paul?” Hell yes. More on the impact of that number in a bit.

And last, but not least: we get to the calls booked rate. We’re going to want two thirds of our interested replies to be booked calls. Thus our 0.66% rate. If we get any lower than 50% of our interested replies being booked calls, we’re in deep trouble. And need to take severe corrective measures.

Now if I were to ask you, among these five metrics, if you had to hang your hat on a single one as your measure for whether or not a campaign was successful: which one would you choose?

The answer I get the most when I ask this directly to my clients in session is, “Calls booked rate of course. At the end of the day, we want to start sales conversations. And the first step in that is getting that intro call scheduled.” And while I applaud this results-oriented inclination, it’s not the correct answer. Calls booked rate can have a lot to do with how quickly you follow up with interested leads, or how you might handle objections and questions over email. The purest indicator of whether or not your message is garnering interest from the market is your interested rate.

So now that we have the metrics we need to be tracking, how does one go about building out an automated email initiative? And how do we leverage our metrics in doing so?

Glad you asked. One principle you want to apply when building out go-to-market initiatives is to not waste good leads on bad copy. With that in mind, the smallest yet statistically significant amount of leads we should start with is 100 leads. With that number, a 1% interested rate would mean we’d get one interested reply.

To those clients that do want to take automated outbound email seriously, we recommend they send out 4-to-6 100-lead test campaigns out on a weekly basis. All 4-steps, deployed over two weeks or less. The idea being that you can get data back quickly. Look at it. Figure out what worked and what didn’t work. And improve your go-to-market motion quickly.

Now, out of those 4 or 6 100-lead test campaigns, you might not get any campaign that hits the 1% interested rate for weeks. But when you do get one that hits that marker, you’re going to want to double down on it. Meaning, you’ll clone it, put 200 leads in there, and then launch it the following week. We’re testing for whether or not it can scale. At times, the campaign won’t. It won’t hit that 1% interested rate marker – in this case garnering at least 2 interested replies. But when it does, you should double down on it again. You’ve guessed it: clone it, load 400 leads in it and then send it out the following week. If you get that 400-lead campaign to hit 1% interested rate, you’ve got yourself a golden campaign; a fully scaled up winning campaign that can be sent out week-after-week to harvest interested replies and introductory calls booked.

Here’s the beauty in all of this: imagine a scenario where you have 5 of these golden campaigns. That means that you’re sending out to 2,000 new leads per week – 5 times 400 leads. At a 1% interested rate, that’s 20 interested replies generated on a weekly basis. At the two thirds calls booked, the bottom line is: you’re scheduling 13 intro calls on a weekly basis. Now you’re cooking with gas! That’s the kind of scalability automated email affords you when executed properly.

Hopefully what we’ve just gone through not only showed the practical way to build out an automated email initiative but also gave you a flavor as to how much rigor, discipline and data literacy is needed to develop a full fledged go-to-market measure. You could apply the same principles we reviewed earlier to different channels and techniques. LinkedIn personalized outbound, Google Search Ads for inbound leads, Content Marketing on X, cold calling to book meetings…all of these and more should work in the same way. Know your metrics and what impacts them. Track them closely. Run experiments. And scale the successful ones.

It’s all great having metrics and messaging. What do we do with all of this when we’re first starting? What experiments should we even consider? How should we conjure them up? If you’re thinking about experiment design, you’re on the right track. We’ll cover what goes into good experiment creation in our next installment. See you soon.

The ingredients lay before you. All chopped up and prepped. Looking gorgeous and fresh. How are you going to make the meal now? What's the recipe for a great outbound message? Well…that's where we start today. I'll be giving you some methods and frameworks on outbound copywriting that take you from rookie to advanced in no time. So, read on. Feel free to take notes. And as always, drop me a line at paul@gassee.com if you have any questions.

Over the past decade, hundreds of founders and startup operators have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the series unfolding in the coming weeks, you will not get only the required frameworks to get you thinking properly about prospecting as a founder. But you’ll get the tools necessary to generate consistent pipeline for your company. So sit tight. Tune in. And, as always, be loud with your questions. Here’s your fourth installment.

Formality kills in outbound copy. And I’m not using the modern slang version of “kills”. No, it murders your outbound copy. Meaning: pronounced dead on arrival in your prospect’s inbox. Before it’s even fully read. The reasons? To start, formality lowers your status in your prospect’s eyes. Your pandering makes you feel inferior to them. Which you want to avoid. In your sales conversations, you want to be the sherpa. The trusted industry expert. The confidant. The person that will guide the prospect through your sales process until the product has been implemented and is delivering value. That role is only possible when your status is a little above that of your prospect. Not coming from below. Addressing your target recipient with a “Dear Sir or Madam” will only start things off on the wrong foot.

The other reason why being overly formal hurts you? It makes the prospect feel like you’re sending them an automated email. Any time we see an overly formal piece of copy, our brains register it as part of an automated effort. The copy hits our retinas, and we’re like, “This message feels so generic and dry. It’s not coming from a human being.” And we press ‘Delete’ or ignore it outright. When you’re less formal, however, and let your personality shine through, we tend to look at the message and ask ourselves, “Could Sophia’s email be one-to-one? As opposed to one-to-many? I could see her writing this herself. Doesn’t feel like AI slop at all.” And when you’ve landed in that camp in your recipient’s mind, you’ve already won. That’s why we tell our clients to write like they would to a friend. Or an internal colleague. Let your individuality show. Your hair down. And allow us to see your quirks. Your idiosyncrasies. Whatever makes you you.

Let’s face it. Even before AI slop was a thing, we were already inundated with dry corporate jargon, business buzzwords and dull copy that made little sense. Anything you can do to stand out will only be to your benefit. So allow folks into the workings of your mind. Let them into your inner world. And reap the benefits of getting more engagement and replies from prospects.

We’ve established the imperative of ridding ourselves of formality. Now, step into this scene of the contemporary workplace, if you could.

Minuscule attention spans. The limited real estate of smartphone screens. And the busy lives of our target prospects. Jake, the Chief Technical Officer at a Series B startup you’d love to sell to, sneaks a look at his iPhone 17 on his lunch break, as he waits in line at his favorite taco truck. He’s coming up for air after wall-to-wall morning meetings, and is finally checking email. Intrigued by your subject line, he clicks on your email. You’ve got a few seconds to capture his attention. With these modern day constraints, it’s no surprise you’ve got to keep your copy super short. Crisp. To the point. With no wasted movement. Zero fluff. Just concentrated essence. Like a morning ristretto. It needs to pack a punch and compel Jake to schedule a quick Zoom call in the coming days.

The point here is: your outbound copy needs to be precise. For a full pitch outbound email, it should be five to eight sentences. Ten at the very most.

And we tend to be long-winded as founders or startup people. We’re proud of our product, that’s been gestating for months. The company we’ve built and its mission. And yet, we must do everything in our power to restrain ourselves. To curb our need to express ourselves fully. We need to find a way to condense what needs to be stated. So as just to elicit the prospect’s curiosity. And invite them to start a conversation with us. Making your copy short is one of the most potent things you can do for your outbound message.

Another powerful action you can take? Pay close attention to your subject lines. And the beginnings and ends of your outbound messages. We tend to focus on the email body copy. Because it feels like the piece de resistance of our communication.

But, in doing so, we forget that our subject lines are pickup lines. You could be the most empathetic, loving partner. But if you’re unable to get the attention of a potential mate sitting across the bar from you, it all doesn’t matter. They won’t be able to experience you as that wonderful person. The same goes for your subject line. You could have the most wonderful email body copy. But without a good subject line that grabs your recipients and entices them to open your email, it’s all for naught. Your email body might as well be blank. One of the bigger topics I coach my clients on is to spend more time on their subject line. Make sure it’s titillating. Curiosity-inducing. That it lures the prospect to click on your email, itching to discover what’s inside. It all leads to more opened and read emails. Which, in the end, gives you a much better chance at more interested replies and booked intro calls.

The beginnings and ends of outbound messages get short shrift but should also be crafted with care. Why is that? Well, because they are often shown in email or LinkedIn messaging clients as “teasers” of the longer message. A good opener in your outbound message will hook your reader. And a good ending will leave them with a lingering impression. If you’re able to make those two bookends crisp and compelling, you’ve got a shot at getting your prospect read on and respond.

Now that we’ve covered the parts of outbound copy that don’t get enough attention and some of the no-no’s when it comes to copywriting, I have a question for you: ever feel stuck when you’re trying to come up with copy?

Well, you’re not alone. It’s a common issue for all of us humans. We stare at our laptops, hands on keyboards, with enough knowledge about our product to make most heads explode. We’ve taken the time to get to know our target market intimately. And we’ve even put together our outbound copy building blocks. And yet, nothing comes out when we’re pressed to produce copy. Like crippling resistance. An intense form of writer’s block. We know we’re got to conjure up something brilliant to catch a prospect’s attention, and we’re all too aware of the constraints at hand. What’s one to do? Well, we’ve got a solution for you.

Rob – our head of outbound & ops – once came up with what we now call the “60-second torture exercise”. Faced with this issue himself, the guy decided to force his creativity by adding another constraint. It might sound counterintuitive, but he was freed by it, believe it or not. It worked so well for him that I was his second guinea pig. I instantly loved this torturous practice so much that we now run all of our clients that want to generate good outbound copy through it. “So, Paul, what’s this torture device you speak of?”, you might ask. Well, it’s dead simple. You pull out a timer. And give yourself exactly 60 seconds to produce the first pass at your outbound email body copy. That’s it! Yes, you’ll get a chance to refine the copy you put down. Perfect it. Take other passes. But the sheer act of adding this time limit allows you to get over yourself. And put that first splatter of paint on the canvas. Freeing yourself from your neuroses. Your self-consciousness. Now, when you do this, it’ll most likely feel like you’ve been thrown in the deep end of the pool. Like it’s an impossible feat. But as time goes on, with more reps, you’ll start to find it manageable. And you’ll produce copy that’s crisp. To the point. Without the fluff that might have been plaguing you in the past. Try it, and as always let us know how it goes.

You now have some method for outbound copywriting. What’s your north star going forward? How do you know if you’re being successful? What to aim for? How to go about improving over time? That’s where we’ll start next week: the metrics you need to track and understand to get better at outbound. And their newfound immense importance to you. Ciao, until next week.

Our previous installment ended with us gaining an understanding for the contrast between personalized approaches and those that are automated. But we hadn’t yet discussed how to actually compose outbound copy. And we had teased that exercise started with conjuring up our ingredients. Our outbound copy building blocks. So let’s dive in.

Over the past decade, hundreds of founders and startup operators have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the series unfolding in the coming weeks, you will not get only the required frameworks to get you thinking properly about prospecting as a founder. But you’ll get the tools necessary to generate consistent pipeline for your company. So sit tight. Tune in. And, as always, be loud with your questions. Here’s your third installment.

For any given vertical you’re going to be targeting, you’re going to want to come up with building blocks for your outbound copy. That starts with deciding who you’re targeting with your outbound motion. You could say, “I’m going after CTO’s at Series B startups.” Or, “We’d like to sell to recruiters at Fortune 500 companies.” Once you decide on an initial vertical you’re aiming at, you’re going to want to come up with at least 10 options in each of the 5 outbound building blocks categories. Why that many? Well, you want to give yourself plenty of ingredients from which to choose to come up with many outbound copy variations. Remember: it’s almost impossible to know what message will resonate until it’s tested in market. We might have opinions or guesses, but until we’ve tried it on prospects, we just don’t know. Giving yourself plenty of building blocks will give you plenty of at bats. (By the way, we’ve developed an outbound copy building blocks worksheet we run our clients through. If you’re interested in getting a copy of it, just drop me an email at paul@gassee.com. Or better yet, reach out and I’ll guide you through it myself in a complimentary coaching session.)

Let’s talk about pain points first. They are by far the most important of all building blocks. “Now, why is that?”, you might ask. Well, there’s an old (not that old, as outbound hasn’t been around for centuries) saying in outbound. That goes something like this, “You get a lot more from leading with pain than you do leading with gain.” And it makes sense, if you think about it. When you lead with something difficult your prospect deals with, you’re showing your prospect you understand them. You are wrapping your arm around them. Empathizing with their day-to-day. This ends up earning you the right to pitch. Versus leading with what makes your product special. That generally turns off your prospect, as it feels to them like you’re trying to shove your product down their throat. As a matter of fact, we’ve written potent copy with our clients that is pretty much just a pain point, and not much else. It’s powerful because you’re able to hit a nerve in your prospect. They feel seen. They open up. And end up leaning in and wanting to engage with you. “If this guy is telling me the truth about being able to solve my hair-on-fire problem, I need to chat with him” is likely a version of what they’re thinking. Next thing you know, you’ve got an interested reply in your inbox. When we’re prompting our clients to come up with pain points, we’ll tell them, “Put yourself in the shoes of your prospect. You’re laying awake at night tossing and turning. What pain in your work life can your product eradicate? If you need to use ‘I’ statements to really inhabit your prospect’s world, feel free to do so.” Good examples of a pain point? “I’m wasting a ton of time on manual tasks.” Or “I’m afraid I won’t be able to deliver our product on time because my technical team is too small.” Or even, “I’m struggling to hire good salespeople and it’s making it hard for me to hit our revenue target.”

Next up: value props. Those are high level benefits your product or service provides your customer. Not a feature or functionality – which is where founders will go a lot of times. People don’t care about those. Or about acquiring a new piece of software. Folks buy outcomes. Pain eradication. Emotions. Feelings. And you have to realize that our inboxes all get invaded with commercial offerings. Thus the importance of having your value props be differentiated. You want to be able to stick your neck out and plainly state “This is how we’re different.” You want your prospect to read your message and think to themselves, ‘I haven’t heard of a product that does this. Wow…feels like a novel approach.’ Example of a good value prop? “Our product is the only one in the market that gives you peace of mind while reducing your workload.” Or, “Customers have reported that our platform has reduced their sourcing time by 66%, more than any other product they’ve tried.”

Quantifiables is our next ingredient. They are all about answering this question, “What is the size of the impact of our solution?” You want to get folks leaning in because they realize how much you can affect their lives. If you tell prospects they’ll get 15mins back per week by using your product, all while asking them for a 10-min intro call, folks might think you have a cool offering. But in the end, they’ll most likely think they can skip having an intro call. 15mins back per week for a 10mins investment just doesn’t move the needle. But, if you told them they get 15 hours back from using your product? That’s almost two full work days. Prospects quickly grok they could be doing a lot with this new time afforded them. Like, spending more time with family. Or working on the golf game they’ve been ignoring for years. One thing we tend to forget too is that human beings process numbers differently. For the example of, “Our customers get 10 hours back per week on average.” You could also express this quantity as: 25% of your week back. Some prospects will feel like 10 hours is more tangible. Others will see 25% as a larger chunk of time. The amount is the same. But folks have different ways of taking in numbers. Relating to them. And what we need to do as go-to-market practitioners is to test both out and see how our prospects react.

What have others said or done that increase our perceived value to customers? That’s social proof. And it’s our next building block. Those can include customer logos, testimonials, case studies, of course. But also things like high-profile investors in our startup. Or press mentions. Or even prominent companies that are in the founding team’s background. “Having just launched 3 months ago, Uber and Google are already customers of ours” might be social proof you’d included in an outbound LinkedIn message. My reaction receiving this as a prospect would be to think, ‘Whoa. These guys have only been in market for three months and already have those logos. They must be on to something big! They’ve got my attention, now...” Next in my mind would be, ‘What are these guys doing that is so good? Perhaps I need to just take a call with them to find out more.’ As you’re already noticing, social proof is your calling card. It’s having other entities than yours telling or signaling to the market that you’re special. Worth paying attention to. And it’s very powerful. So, when putting it together, get in your prospect’s skin. What would impress them most? What would have them quickly go from discarding your email to saying to themselves, ‘Man, this company is working on something worthwhile.’ Remember, as an early stage startup, we don’t have the benefit of an established brand or of marketing air cover. If you get an email from a rep at Salesforce, you’ve got a story about them. Perhaps it’s ‘most successful CRM of all-time, Salesforce tower in San Francisco, Marc Benioff.’ If you received a LinkedIn message from a salesperson at Apple, you might think, ‘Steve Jobs, the iPhone, Tim Cook.’ You have a narrative about the tech giant there too. As nascent startups, we’re mostly an unknown quantity. Putting yourself on the map with great social proof changes the way you’re perceived.

For our last ingredient? The call-to-action/offer. A critical component that generally doesn’t get enough attention from founders. Despite the fact that it has shown to be the difference from a lackluster outbound campaign to one that takes off. Generally, founders will have a “quick 15min call” or a “product demo” as their CTA/Offers. And those should be tested. But you have to realize that a lot of prospects receiving an outbound message from you will still be sitting on a razor’s edge about taking an introductory call with you. Before your message, they most likely hadn’t heard about your company or product. You might have sent a crisply worded 5-8 sentence message. But there’s a great likelihood your recipient is thinking, ‘Boy, this product sounds cool. And I could probably use it. But, man am I busy right now. Not sure we could even implement it.’ That’s where you need to deliver even more immediate value to your prospect. What above and beyond your product can you offer your prospect in the 15-min call they’d be taking with you? What can you dangle that would have them say a sure fire “yes!” to joining you on a Zoom? The answer to that question unlocks a whole lot of interested replies. Follow me down this fictitious rabbit hole for a second. Let’s imagine that instead of selling your current product, you’re peddling a SaaS tool for sales coaches. I know I know…I did ask you to come with me to this made up place. But let’s imagine you composed the following message:

Hey Paul,

Are you struggling with menial tasks?

If so, we should talk. We’ve spent the last two years building a product that should completely eliminate those. The average sales coach using us gets 15 hours back per week.

Have 15mins for Zoom in the coming week to see if there’s a fit?

During that call, we’re more than happy to share the top pitfalls sales coaches fall into that prevent them from making their highest possible income. These have been amassed over the 200+ conversations we’ve had with sales coaches like you over the past two years.

Cheers,

[Founder]

Now, I consider myself a top sales coach. But I’m not arrogant to think that I might not learn about one or two pitfalls I’m falling prey to. And that just by bringing those into my awareness could have a 5 or 6 figure impact on my business. All of a sudden, I go from reading this email and thinking, ‘Wow, this is a cool tool…I could potentially use it. And if they’re quantified impact is true, I might be able to do a ton with this gained time.’ To, ‘The tool sounds great. But I need to take this call. Regardless of whether or not I can use it, I could learn something super useful from this founder, that could have a significant impact on my business.’ I’m no longer straddling the fence, but taking the intro call ASAP.

You’ve got your ingredients for outbound copywriting. And they’re beautifully prepped. The “mise en place”, as chefs call it. Now how do we create a tasty meal from those building blocks? That’s where we’ll start next week. I’ll do my best to deliver best practices in outbound copywriting. See you then.

Okay…we’re back. Our last episode covered why prospecting can feel rough. Why it’s not given enough attention and resources. The characteristics of inbound and outbound. And a rule of thumb for when to consider automation in your outbound motion. But we never really got to contrast more manual outbound approaches with industrialized ones. So let’s get to it.

Over the past decade, hundreds of founders and startup operators have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the series unfolding in the coming weeks, you will not get only the required frameworks to get you thinking properly about prospecting as a founder. But you’ll get the tools necessary to generate consistent pipeline for your company. So sit tight. Tune in. And, as always, be loud with your questions. Here’s your second installment.

Your two options in outbound are automation and account based marketing – also known as ABM. Account Based Marketing is a fancy-way of saying personalized outbound. You hand-select accounts you’ll be reaching out to, and find personalized ways to break into them. And initiate sales conversations with key stakeholders within those organizations. Some folks talk about their Dream 100 list. This refers to the top 100 accounts you’d like to start selling to. The customer logos that have you salivating for your startup. Building such a list is a great way for any startup operator to start their outbound motion. It dials in your focus and – when successful – allows you to build sturdy social proof. Envision being able to say, “Our product launched just 3 months ago, but Uber and Google are already customers of ours.” Stronger case for folks to pay attention to you, wouldn’t you say?

But back to personalization. Put simply: it increases your response rates. “Why?”, you ask. Well, because you’re gifting your prospect the feeling of being seen. Understood. Every human being has the innate desire to feel like they’re seen and accepted in their own uniqueness. As a salesperson, you’re tapping into that need when reaching out in a personalized way.

When you take the time to notice that your prospect has been to your favorite omakase sushi spot in San Francisco, you not only establish a kinship around your mutual love of delicious raw fish, but you also make them feel known. And you, in turn, get rewarded with a higher reply rate. Personalization also has the advantage of making each outbound message very different from the previous one. Which can play a huge role in keeping you out of spam. Remember: spam algorithms from companies like Microsoft and Google look for carbon copies of messages being sent out by the same inbox. And then penalize those senders for their carpet bombing. Personalization is the opposite of that. Each personalized message feels unique, and thus is very spam-friendly.

Account-Based Marketing also has a shorter time-to-value – namely obtaining interested replies – than automation. The explanation for that? As we just mentioned, when you send personalized messages to prospects, your response rates are typically higher. And those response rates will also often pull up interested reply rates. Think of it this way. Anytime you’re personalizing, you’re giving yourself a chance at a longer conversation. You’re driving up engagement. Your prospect is more likely to linger on your message and give the sales copy portion of your message a greater chance to land with them. So when done correctly, you’re getting your first few interested replies faster with ABM than with automation.

Here’s an email you could send me that would almost guarantee yourself a response, provided I saw it:

Subject Line: hot yoga in India, Paul…?

Hey Paul,

Couldn’t help but notice that you were a fervent yogi…have you considered doing a retreat in India?

[Sales Copy]

BTW: do you think Djokovic has a shot at breaking through for more Slams with Sinner and Alcaraz dominating the Men’s game right now?

Now, why would this way of personalizing strike a chord with me? Well, I started doing yoga over 10 years ago, on the advice of my late therapist Riyaz. My close friend Austin had been trying to drag me to Bikram yoga classes. In one of our sessions, I asked Riyaz what he thought of my taking up this new discipline. To this day, I remember how emphatic he had been. “Yes, you should!” was his directive. More than a decade later, I’m good for one to three yoga classes per week depending on the season or mood. It’s become an integral part of my life. Among other things, yoga has reduced my anxiety, improved my flexibility and helped slow down my mind.

So you seeing me as a yogi – and thinking that perhaps I’d be interested in doing a retreat at the practice’s birthplace is sure to elicit some emotion from me.

Now to the closing piece of personalization bookending the email. I grew up playing competitive tennis. I don’t play much anymore, but I follow the men’s professional game very closely. You calling out a major dynamic happening at the top of the men’s game – the elder statesman Djokovic staving off Father Time as he tries to break through Sinner and Alcaraz’s dominance – and asking my opinion about it is a sure fire way to get me leaning in.

Having read the message, regardless of what is being pitched, I’m going to think, ‘Man, this person gets me. They’ve taken the time to truly understand what’s important to me, what I care about. I owe them a response at the very least. Whether or not their product is relevant to me.’ And that’s exactly the kinds of thoughts you want your prospects to have when they receive a personalized outbound message from you.

By the way, this is how we teach personalization to many of our clients. A personalization layer at the top of the email to break the ice. And then one, as you bid them farewell, post call-to-action/offer. We’ve noticed that getting a least two in per email greatly enhances your chances at a response from folks.

Before leaving you this week, I’d like to illustrate how you should start thinking about automation or manual approaches with two extreme examples.

First, let’s imagine for a second that you were selling a product with an average ACV (average contract value) of $2M that was a fit only for Fortune 100 companies. And because of the nature of your offering, the only two job titles you’d want to target are the CEO and the CFO. That’s a total of 200 – 100 total companies times 2 job titles – possible contacts to go after. Due to the large average contract size and low number of potential targets, you could spend a huge amount of time and resources personalizing your outbound communications to each individual lead. ABM is perfect for that. I’d applaud a founder that would want to spend 2 hours crafting a handwritten message on parchemin paper that was to be delivered by private carrier. Or a startup operator that was to send one Air Jordan to a prospect with a penchant for sneakers with an accompanying note saying, “This is my way to get my foot in the door. The other shoe will drop when we meet in person 😉.” The key is: each introductory meeting booked is worth a lot to the startup selling here. Definitely worth wringing the towel dry to initiate the sales conversation.

By contrast, let’s now picture you’re targeting finance leaders at startups to sell them a product with an AVC of $12K. Doing a quick search in Amplemarket – our favorite marketing automation tool – for such leads shows us a total of 432,456 target contacts. For that vertical, automation fits like a glove. You’ve got a veritable ocean of prospects to go after. Because of the abundance of leads and low ACV, you can take full advantage of what automation has to offer. Namely, the fact that it’s a lot less resource-intensive. You could write up an automated email campaign, fill it up with leads, and send it off within 30 minutes.

For account-based marketing, our clients will generally spend 15 minutes sourcing a lead, researching it, and writing a personalized message before pressing “Send”. Automation is also far more scalable. In a matter of five minutes, you can clone a successful campaign and double down on it with twice the leads you had used in the initial sequence. And lastly, because of its scale, you’re able to get to statistical significance faster. Within 2-weeks, you can have a 4-step 100-lead campaign fully deployed and come to some conclusion on the messaging it contains and the persona you're targeting. Account-based marketing doesn’t afford you that kind of statistical significance until you’ve put in a lot of work. Usually in the hundreds of messages sent out. At fifteen minutes per message crafted and sent out, that’s a bunch of time spent before being able to deduce much of anything from your laborious outbound efforts. I’ll let you run the math.

Now that we’ve covered our large scale options to put forth good outbound, how does one think about crafting a message to garner interest from a target prospect?

Well, the first thing to consider are the ingredients for this messaging. Just like it’s virtually impossible to make a great meal without good ingredients, it’s out of the question to compose a great message without good outbound copy building blocks. They fall in five different categories. And you’re going to want to have one from each category included in an outbound message designed to be a full pitch.

That’s where we’ll pick up our discussion next week. Join me as we review the five ingredients that enable you to make a delectable outbound message. You’ll leave prepped to start copywriting.

Prospecting can feel overwhelming, as a founder. Because you don’t know where to start. Or how to tackle it. There’s an ocean of things you could be doing. And yet, you’re constrained by the resources at hand.

But overwhelming also because you need to figure it out. Fast.

Your company’s life depends on it.

Top-of-funnel activity is the lifeblood to your revenue. The oxygen to your startup’s lungs. The gas to your sales engine. Without it, you can just stick a fork into the idea of having a company.

And yet, prospecting doesn’t garner the attention it deserves. It doesn’t get enough love. Founders are quick to ignore it. Sweep it under the rug. Delegate it out to junior employees. And part of me gets it. The work is far from glamorous. Like eating glass. A lot of times, we’re sending messages out into the void without getting any replies. There’s no dopamine to keep us going.

Many founders undervalue the time and resources it takes to get to message-market fit. They end up flailing at it without much discipline or structure. Months of precious runway go by while the pressure keeps mounting.

Know what I mean?

Over the past decade, hundreds of founders and startup operators have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the series unfolding in the coming weeks, you will not get only the required frameworks to get you thinking properly about prospecting as a founder. But you’ll get the tools necessary to generate consistent pipeline for your company. So sit tight. Tune in. And, as always, be loud with your questions. Here’s your first installment.

Alright, I won’t keep you waiting. Let’s jump into the strategy of getting in front of potential customers.

There are exactly two ways to get in front of customers: inbound and outbound. Inbound is defined by potential customers coming to you. Outbound is the opposite. You go out to your prospects.

Quick detour into the world of football – which is front-of-mind this time of year. If you follow the game, you may already know that an unstoppable football offense will often consist of a stout running game and a potent passing attack. If one is slowed, or thwarted, the other can pick up the slack and carry most of the offensive load. The same is true for prospecting. Overnight, your inboxes could end up in spam hell, leaving your outbound compromised. But your content marketing still stands and keeps bringing in leads thanks to your thought leadership on LinkedIn. Or, a competitor having raised a mega Series B might start outbidding you on keywords, driving your inbound cost-per-lead skyward. You pause Adwords campaigns to figure out your next move. All the while, your LinkedIn automated campaigns keep you afloat by striking up conversations with your target prospects: recruiters that spend every waking hour on the business social network. The point is: if you want to derisk your startup, you need to get really good at doing both outbound and inbound.

Each has its advantages and pitfalls. Inbound feels great because leads are coming at you. It’s like being the pretty girl at the bar. You get approached. And the attention feels intoxicating. Because leads are coming in hot, with high intent, you could drop the ball, and often they’re the ones following up with you to make sure a demo or introductory call is scheduled. These leads also tend to be further along their purchasing journey. They’ve experienced enough pain that they’ve taken the time to research potential solutions. In doing so, they landed on your website and have started getting acquainted with your product. You’re far from an unknown quantity. Some background has been obtained. They’re leaning in, and want to find out more.

The issue with inbound is that it’s hard to control who comes at you. And with that, you’ve got to learn how to qualify hard; keeping the riff raff out of your pristine pipeline. Tire kickers might be coming to your car lot. But you need to find a way to figure out if they’re real buyers.

Outbound, on the other hand, gives you complete control over who you’re targeting. Which is powerful. The trick is garnering a prospect’s attention. As your outreach is an interruption in their day. They might not know you even exist. And perhaps haven’t even considered they’re suffering from the pain you’re promising to eradicate.

Having said all that, outbound is easier to scale early on. And your time to value – in this case generating meaningful customer conversations – is shorter. Some startups are able to unlock inbound early on in their journey. They might strike a nerve in the market and get prospects to tune in and reach out. Or they might be able to get their ads to resonate with their audience. But in the greater majority of cases, inbound is harder to crack in short order. With runway constraints and pressure mounting to get traction, it’s the more risky path for founders.

Outbound allows you to – among other things – get fast feedback, unearth early objections, test messaging, and validate your ICP. Because you’re going into the market. And you’re not waiting around for it to come to you. To get your initial batch of customers, outbound is generally – although not always – your better bet. That’s where we’ll narrow our focus going forward.

Now, let’s look at market size. Number of target contacts, specifically. In outbound, the number of contacts you have will help dictate what strategies and tactics you’ll employ.

And there’s a rule of thumb you’re going to want to use: if you have at least three to four thousand contacts in any given vertical you’re targeting, automation should be considered.

“Now, why is that, Paul?” you might ask.

Well, the beauty of automation is that you can use it to scale your efforts. Hard. Whether it’s automating your emails, LinkedIn exchanges, or even power dialing, your ability to automate outbound gives you greater muscle and incredible efficiency. But getting to message-market fit with automation can take you quite a while, and quite a lot of contacts.

For automated email, as an example, it might take you fifteen or twenty one-hundred lead campaigns to come up with three campaigns that are working very well. That’s a total of 1,500 to 2,000 leads used to land on those few campaigns you get to scale up. Which then only leaves you 2,000 to 2,500 leads to work with. At 400 leads per fully-scaled up winning campaign, you’ve got 5 of those scaled up campaigns before you’ve chewed through your 2,000 remaining leads.

So all in all, having more than 3,000-4,000 leads to target gives you room to scale. But being anywhere below that plateau won’t make automation even worth doing.

So, if we’re not going to automate, what are our other options? Shall we just reach out to people in a more manual way?

That’s exactly where we’ll start in next week’s episode. We’ll explore the differences between more manual approaches and automation. And how to think about using each method. See you then.

Over the last 9 plus years, hundreds of founders have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the next few months, in the form of weekly episodes, we’ll be looking at the top startup sales misconceptions folks possess. And how I get them to think instead. Reading this series will make you smarter and more aware than most startup operators, as you’ll already know how to think about go-to-market and sales, and avoid some of the biggest pitfalls. Consider this your cheat sheet in shaving months off your revenue growth journey. Here’s your tenth and final installment. Read on.

“But Paul, we can’t really go after these leads until we know what we’re going to tell them.”

Or, “I’m afraid that we’ll burn this lead. It’s a hugely valuable account for us. I don’t want them to get put off by our message.”

These are comments I get all the time from clients. There’s a great fear. That sending the wrong message to the right contact will burn that lead forever.

And, yet, that fear is unfounded.

Listen, whether it’s for my own outbound, or when building it with clients, I’ve seen a wide array of replies from prospects. Including some of the more negative ones you might ever imagine. One instance still sticks in my mind. A prospect took the time to take a picture of himself flipping me the bird. And, to this day, it makes me laugh.

Now, even with this “gentleman”, if we were to ask him a few months out, “do you remember the brand or company that wrote you that cold email, where you got upset?”

I’d bet you he’d say, “No, not anymore. I wish I did remember them. God, they pissed me off that time.”

And this was a man who was very deliberate in making his sentiment known. A guy who was seemingly very angry at our cold approach.

Everybody you send a message to when it comes to outbound will more than likely not remember what you said to them just a few days later. Yes, this may be hard to believe for most of us. Our egos want our message to matter. To make a mark. To be meaningful to our targets. We want it to establish a positive connection and get us that introductory call booked.

At times, we get there. The message gets the desired reaction. And a sales conversation blossoms from it.

A lot of times, our message gets ignored. Partially read. Or even stared at thoroughly. Re-read several times. And then left unresponded.

That’s just the nature of the beast. Outbound is a numbers game. And getting a 1% interested rate on automated outbound is considered great.

Now, do I understand that fear? Why folks might be terrified, as they type out their cold email to a target that could be worth 6-figures?

Of course I do. There’s a huge amount of perceived pressure there. You might think that any misplaced syllable could doom your chances of garnering that initial meeting. ‘What if the prospect doesn’t get what we offer with our product? What if I’m not able to communicate that I understand their problem I’m here to fix? Goodness, this may be my only shot to get them to pay attention. I need to make the best possible impression here.’ A river of thoughts swirling through your mind, as you sit at your laptop trying to formulate your cold email.

But reality for the recipient looks a lot different. We skim our email or LinkedIn inboxes quickly. What doesn’t grab our attention, we’ll ignore in the snap of a finger. The messages that come from strangers – we’ll usually spend a split second on. Not recognizing the sender’s name, it takes a lot more copy-wise to get us to linger. Even if we happen to spend thirty seconds reading an email. And get turned off by it. What happens most often is that we move on. Swiftly to other items on our to-do list. By the time we get into our cars on the way back from the office, that message that pricked us is a distant memory. Our thoughts are now focused on the kids we’re about to see. On the warm hug we’ll get from our spouse. Or on the meal we’re about to savor on date night with our significant other.

Whatever upset we felt in the middle of our day because a software salesman clumsily pitched us his product over email is now the smallest blip on our radar screen.

I’m here to tell you to get over yourself. Do your best. Learn the best practices. And let it rip.

If you don’t get an interested reply, you will get other at bats. Shots on goal. Opportunities to cut through the noise and garner your prospect’s attention. You can reach out several weeks later, and pretty much be sure they won’t remember the initial email you’d sent. And even if they did – it’s very unlikely they’d be angry at you for it. We’d ensure you compose copy that is both inoffensive and value-laden. Remember: you didn’t commit a crime. You simply reached out to a stranger, because in your heart of hearts, you believe that they’d be better off with your product in their hands.

If you enjoyed this series, do me a favor. Well, maybe two.

Going forward: examine your beliefs about sales and go-to-market more closely. Be willing to challenge and refine them by confronting them to reality. This takes more guts and a lot less ego that you might imagine.

And two: collect some misconceptions you’ve uncovered in startup sales and send them to me. Who knows? They might fuel the sequel to this series 🙂.

As always, if you ever need support on any front, reach out via email at paul@gassee.com and book a free consultation with me. 1-hour. You bring your sales/GTM challenges. I do my best to help you solve them. Chat with you soon.

Over the last 9 plus years, hundreds of founders have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the next few months, in the form of weekly episodes, we’ll be looking at the top startup sales misconceptions folks possess. And how I get them to think instead. Reading this series will make you smarter and more aware than most startup operators, as you’ll already know how to think about go-to-market and sales, and avoid some of the biggest pitfalls. Consider this your cheat sheet in shaving months off your revenue growth journey. Here’s your ninth installment. Read on.

“I’ve been studying our target persona. I know what works and what doesn’t with these prospects. You have to listen to me.”

Or, “I’ve worked this channel in go-to-market for a long time. I know what I’m doing here.”

Or even, “I never answer cold emails. I just hate them. There’s no way this is going to work with our market.”

These are comments I get a lot from clients I work with or startup operators I get to meet.

There’s nothing wrong with drawing on experience to draw conclusions about the world. The problem lies in having that be the only input. Or fervently holding onto beliefs that don’t appear to work for us.

We’re more than allowed to have our own perspectives. Our biases. Our ways of viewing the world. The issue arises when we close ourselves off to other perspectives. Or to the possibility that reality could be different from what we initially thought.

I can’t tell you how many times I’ve been humbled in the discipline of go-to-market. Things I thought ended up being dead wrong. Or beliefs I held kept holding me back.

One example came to mind when I was thinking about writing this piece. Years ago, a premium co-working space approached our consultancy for marketing help. They wanted to build out their automated email initiative. This office space provider had a desirable client base, gorgeous ergonomics and design in premium locations across the city. They were looking to acquire clients by getting the word out to startup operators who wanted to work in an inspiring setting. The offer we put forth was an opportunity to tour the stunning offices. And have a go at working at one of the three locations for free for a day.

Several weeks into our engagement, the leaders of the co-working space suggested we include beautiful pictures of their locations in the emails we were sending out.

All of my previous experience screamed a resounding “No!”

Anytime we had included pictures in automated outbound emails had been duds. Emails were too heavy. They often ended up tripping spam filters. And recipients didn’t like us clogging up their inboxes with these large messages.

So why would this even work?

I understood that we’d showcase the elegance of these offices. But I couldn’t bring myself to believe that including photos was going to be worth it.

After the initial sets of campaigns ended being mediocre. And the owners of this coworking space kept pushing. I finally relented.

“Let’s give it a go. Don’t think it’ll work. But we owe it to ourselves to test it out. Our campaigns haven’t been very successful so far. We have nothing to lose.”

Can you take a guess as to what happened next?

I was humbled.

Surprised and thrilled. All at the same time.

Our automated email campaigns took off. And soared. Our prospects were booking a ton of free tours. And we were generating foot traffic.

Our client was thrilled. We count them as a hugely successful case study.

And yet, all of this success probably wouldn’t have happened, were it not for them insisting. I had to put my ego – and previous experience – aside, and launch the experiment. Without knowing whether or not it would pay off.

The market spoke. As it turned out, prospects wanted to see glossy pictures of the office space they’d inhabit someday. And we all won out.

Eating humble pie is all part of the job as go-to-market folks. I welcome it now. I try to challenge my own assumptions. Beliefs. And lessons from past experiences. Just because I learned something in the past doesn’t mean it’s still applicable. Or that it doesn’t deserve to be questioned. Or refined. We all should remember: our experience – at the end of the day – is very limited. N of 1. Even for those of us that have seen a lot. And new inputs should have us draw new conclusions about the world. We need to be okay with that. And accept it, even.

I’ve seen founders and startup operators hold on to their beliefs for dear life. Not wanting to even allow for the fact that reality might be a bit different than what they previously imagined. I had a founder a couple years ago hold onto his vision of only wanting to do product-led growth. After over a year of optimizing his inbound flows, and only when left with six months of runway, he decided to hire me because his revenue numbers were not moving up and to the right fast enough. I’ll let you guess what ended up happening to his startup. Just the other day, I did a consultation with a founder who was convinced that outbound email should in no way be part of her go-to-market, because she hates “receiving cold email, and I haven’t ever responded to one in my life.” When I asked her, “Have you considered that you might be different from your target market? Or that your opinion only represents the views of one person?” She finally replied, “Maybe we should try it.” I’ll take my victories small when I can get them.

Perhaps Socrates offered us the most worthwhile lesson when it comes to go-to-market – and life in general, when he uttered, “I know that I know nothing.”

When devising GTM experiments with clients in session, they’ll often ask, “Do you believe this will work?”

My advice often takes the form of, “I don’t know. But we owe it to ourselves to try it.”

Next week, in our last installment of this series, we’ll dispel a belief that prevents many startup operators from reaching out to prospects.

Over the last 9 plus years, hundreds of founders have come to me for coaching on their sales and go-to-market challenges. And I've done my best to help. In the next few months, in the form of weekly episodes, we'll be looking at the top startup sales misconceptions folks possess. And how I get them to think instead. Reading this series will make you smarter and more aware than most startup operators, as you'll already know how to think about go-to-market and sales, and avoid some of the biggest pitfalls. Consider this your cheat sheet in shaving months off your revenue growth journey. Here's your eighth installment. Read on.

“Let's do product launches on HackerNews and ProductHunt to get leads. We'll also ask for customer intros from folks we know and from our investors to get ourselves some pipeline.”

There's nothing inherently wrong with the above. By all means, do it all. Grab that juicy low-hanging fruit and take a big bite out of it. You won't hear me stopping you, as your coach.

And yes, doing those things will probably yield early easy leads. And maybe even some initial customers. A bit of revenue.

However, like a ton of low-hanging fruit. It can be overly tempting. Alluring even. And take you away from the unglamorous fundamentals that will take your startup places.

Doing the above exclusively can put your startup in a world of trouble. And it usually comes from a place of scarcity and urgency.

You have very few leads, and you're hoping to find some quick wins to generate some much-needed pipeline.

It usually feels a lot better getting leads that come inbound. You feel like the pretty girl at the bar. You don't have to face much rejection. You're getting plenty of attention. And when you get intros, folks come in as friendlies. They'll gladly take that call with you.

What I do ask my clients to do however is to take a step back, and take a more long term view. I'll inquire, "What happens when you've got these launches, and depleted your network with intros? How are you going to scalably grow revenue?"

The silence gets deafening.

"What we should be doing concurrently to those short term spiky tactics is to uncover GTM channels, tactics, and messaging that will get us leads in a scalable way. We should be seeking message-market fit."

Message-market fit – as many in these parts know – is a component of product-market fit. Some even say: its most external part. It's the ability to put a message out in the market and have it respond with interest. And get a sales conversation started.

And it usually takes hard work. A lot of it. Sometimes past what you think you can give. Without much dopamine to keep you going. It's what makes go-to-market such a grueling discipline.

There are two major scary parts of not engaging in real go-to-market to uncover message-market fit.

Let's look into the first. Getting intros from YC batch mates feels wonderful. Friendlies will not give you much opposition. And usually they'll be more than receptive to giving your product a try. Getting on a free trial. And even purchasing past that, without much resistance, if the ticket size is on the smaller side.

“Paul, why would that not be a good thing?”, you might ask.

Well, friendlies are incentivized to be nice. And thus won't give you the brutally honest feedback you should be craving. As a founder doing sales, you should relish the opportunity to learn from every market interaction. Particularly if the learning is not silky smooth. Especially if it contains bitterness. Grit. Rough edges.

You should be leaning in. Welcoming the difficulty. And asking for more. Those are the lessons for you to harvest. And examine carefully.

The learnings you'll get from strangers that have responded to a cold email are infinitely more valuable than the agreeable interactions and signed deals you've garnered from the customer intros your VC tee'd up.

Prospects will let you know what the market really thinks of your product. You'll get things like, “Hmmm…this isn't the right time for us.” Or, “Your product feels like it could be useful, but I'm not sure I want to rip out what we currently have.” Or even, “We've decided to go in a different direction.”

Versus, “Hey, what you guys have built is awesome. Happy to take it for a spin.” Or, “When Sarah makes a recommendation, I listen. She's never led me astray. Would love to see what you guys are building, and see if it might make sense to partner.”

Feel the difference?

The second major frightening part of not doing real go-to-market? These spikey go-to-market tactics are not scalable. And not reliable long-term. Even the greatest networks deplete over time. Which means that intros to relevant portfolio companies will eventually dry up. And your ProductHunt launches? While good to generate an influx of inbound leads. They are not something you can do week after week. I can't tell you how many startups I've either worked with or met that had little to no pipeline coming through after they had exhausted their low-hanging go-to-market tactics. And because finding message-market-fit can take six to twelve months for some startups, they'll plateau at a revenue number for months. Only then do they feel forced to dedicate the time and resources to figuring out how to generate interest from the market.

What's the simple cure to these months of barren pipeline?

Getting started with the non-glamorous hard yards of real go-to-market as early as possible. Concurrently to the facile GTM tactics. So that you can start making headway towards message-market fit, as you benefit from those early spikes of leads. Hopefully preventing any interruptions in lead flow in your startup's journey.

Next week, we'll explain why humility and open-mindedness are critical qualities to cultivate in order to be successful at go-to-market.

Over the last 9 plus years, hundreds of founders have come to me for coaching on their sales and go-to-market challenges. And I've done my best to help. In the next few months, in the form of weekly episodes, we'll be looking at the top startup sales misconceptions folks possess. And how I get them to think instead. Reading this series will make you smarter and more aware than most startup operators, as you'll already know how to think about go-to-market and sales, and avoid some of the biggest pitfalls. Consider this your cheat sheet in shaving months off your revenue growth journey. Here's your seventh installment. Read on.

“I don't have anything in common with this person. How can you expect me to personalize my message to this prospect?”

Just the other day, I was sitting with a client. We were looking at a prospect, and I was suggesting he might be able to personalize his outbound email by using this prospect's collegiate athletic career.

“Paul, I can't relate to him playing competitive volleyball. And being an all-American and MVP.”

“What do you mean? You've never played volleyball?”, I replied.

“Well, a little bit in middle school. But that's about it. I really don't feel qualified on the topic. And it might feel like a stretch to mention that we have that in common.”

I can't tell you how many times this issue pops up in my coaching with clients.

Quite a few founders and startup operators feel like they need to have something in common with their prospects in order to personalize at all.

And I'm here to tell you that's a limiting belief. It sets the bar too high. And it prevents folks from personalizing well. Or even at all.

Now, is it more potent to personalize with a tidbit you have in common with a prospect? Of course. I'd be lying if I said otherwise. Having something in common with the person you're reaching out to tends to establish an instant kinship. It not only makes the person feel seen. But also says, “Hey, we're part of the same group. We're cut from the same cloth. You and I are similar. We should be talking.”

But limiting yourself to things in common will only curb your personalization. Some LinkedIn profiles are very sparse. Some prospects don't have much of a digital footprint. What you might end up with to pick from might not include anything you perceive as a commonality.

So what do you do then?

Dale Carnegie had our answer, way back when. “You can make more friends in two months by being interested in other people than you can in two years by trying to get other people interested in you.”

Be interesting by being interested.

Remember: with personalization, we're trying to make the other party feel seen, heard and understood. A deep human desire we all possess. When you make a person feel seen, they feel special. And are compelled to reply to your outbound message.

With good personalization, you aim to increase your reply rates, which in turn has a chance to pull up your interested reply rates.

But none of that says that you need to have anything in common with your prospect. You just need to let your curiosity lead the way. What do you find fascinating about your prospect? What makes them unique? What do you think they're most proud of?

If you can express genuine interest in those parts of themselves, more often than not, you're going to unlock a connection with a prospect.

Let's work with the instance we mentioned above. My client didn't feel like they had played a sport at a high enough level to comment on it. Or to even relate to it on a deeper level.

I nudged him a bit. “What if you asked him about All-American collegiate volleyball career? And how it contributed to his success in business? Perhaps he picked up lessons that enabled him to really soar…”

“You're right, I could definitely do that. Let's write it together.”

We came up with something like this.

Couldn't help but notice that you had crushed volleyball back in college…what lessons did you pick up during that time that have contributed to your success in business?

We took the liberty to make a link from his starring in a college sport to his outstanding career in business. My client exhaled. He didn't feel out of his depth. Or that he was speaking out of context. All he did was lead with genuine interest and curiosity.

An additional note on personalization: the more specific you make it, the better. Meaning: the more you get to what makes a person unique, the more they're going to feel like you understand them.

Let's imagine for a second that you had spent a few years in your mid twenties in New York City. And that you wanted to reach out to me cold, to sell me your product. In thinking about how you were going to get my attention, you looked up my LinkedIn profile and found out that I too had spent the first couple years of my career in Gotham (not the truth; I was actually in Paris).

You might decide to personalize the beginning of your email to me like this:

Subject Line: hello from a fellow former New Yorker 🗽

Hey Paul,

I noticed you had spent the first couple of years of your career in New York (I also did in my late twenties)…how cool was it to be young in that town? The intensity and liveliness of it was intoxicating to me. I never felt bored.

Now this is what I'd call decent personalization. Just north of mediocre. But far from spectacular. You're trying to connect with me about living in one of the largest metropolises on the planet. 5 boroughs. A city of more than 8 million people. But it lacks a lot of specificity. I might feel a little anonymous – which interestingly is how people feel in large cities like NYC – if I received this message.

Now compare it with this bit of personalization below.

Subject Line: working out of Williamburg 🍕

Hey Paul,

I saw that you worked out of Billyburg the first couple of years in your career. I happened to be in NYC too (lower Manhattan more specifically) in my late twenties. You ever go to Macolletta? Wasn't their Margherita pizza just amazing (sauce super fresh, and crust perfectly puffy)?

Now this one above is very good. You've gone from talking about a metropolis to the specific neighborhood (Williamburgh) within a borough (Brooklyn). You even zero'd in on a great pizza joint I may have gone to. Or heard of. You're using NYC jargon – “Billyburgh” – to identify Williamsburg. Finally, you blended our commonality of being former New Yorkers, with genuine interest in my unique experience within a smaller subsection of Gotham.

Feel the difference?

Good. Now get out there and personalize to your little heart's content.

Remember: there's no need to have anything in common with your prospect. All you need is genuine interest and curiosity. And an ability to verbalize it.

Next week, we'll discuss that, while tempting, low-hanging fruit is not the most important thing to focus on in your go-to-market.

Over the last 9 plus years, hundreds of founders have come to me for coaching on their sales and go-to-market challenges. And I've done my best to help. In the next few months, in the form of weekly episodes, we'll be looking at the top startup sales misconceptions folks possess. And how I get them to think instead. Reading this series will make you smarter and more aware than most startup operators, as you'll already know how to think about go-to-market and sales, and avoid some of the biggest pitfalls. Consider this your cheat sheet in shaving months off your revenue growth journey. Here's your sixth installment. Read on.

“We plan on asking our customers what they'd like to accomplish in the free trial or pilot period.”

Have you ever looked at reviews for restaurants you've been to before? Am I the only one with that weird habit?

I know I'm an oddball, but go ahead and do it.

You'll find a few surprises, I'd be willing to bet. I've always been dumbfounded by some of the reviews I land on.

“This omakase was not worth the money and I was still hungry leaving the restaurant.”

“The waiter we had was snooty and the pasta lacked flavor.”

My experiences at those restaurants couldn't have been more different. The reviewed sushi spot was one of the best I'd ever been to. And the described Italian restaurant delivered an elaborate pasta tasting menu at their chef's counter.

What I've come to realize is that people's opinion of the same product or service can vary greatly. Based on numerous factors. The lens through which they look at life. Their relationship to money. Their current mood. The quality of their day leading up to the experience.

What some interpret as pretense. Others consider elegant. What some view as refined. Others see as finnicky. What some experience as delicate. Others perceive as dull.

The point here is: when we rely on people's feelings, it's hard to get to a singular view on the same experience.

So if you allow folks to tell you what they'd like to accomplish during a free trial or pilot, you run the huge risk of getting many different answers. And find yourself running around trying to satisfy very different expectations.

Not a role you want to play.

Flash back to my time at Whitetruffle. When tasked with figuring out our sales model, I initially didn't know what to do with our credit-card activated free trial.

‘How was I to make sure that we converted a large chunk of our trials into paid customers? Was there anything I could do to set the right expectations? Expectations we'd clear often and that also felt valuable to our customers?’ I asked myself.

I desperately wanted to find a way to control the sale. Folks would convert automatically through the magic of credit card processing, if they felt satisfied. And thus, I felt we should set a narrative for success that would lead to customer satisfaction.

The first place I turned to was our analytics dashboard. If ARR/MRR was our number one company metric. A close second was introductions. Quick refresher: Whitetruffle was a tech talent sourcing platform. We called ourselves a “dating site for tech talent”. Leveraging an algorithm that took in fifty plus core signals, the platform would match tech candidates – software engineers, product managers, UI/UX folks and designers – with companies looking to hire them. Employers – who were our paying customers – would get daily matches. Any match they would say ‘Yes’ to would receive a message, asking “Yelp is interested in chatting with you. Do you want to get connected to them?” If the candidate responded, ‘Yes”, an intro was made through the website.

Classic double opt-in. Introductions were a critical metric because they were an indicator of the marketplace's liquidity. The more introductions we'd deliver, the more value candidates and companies were getting from Whitetruffle.

I started taking a look at the number of intros we were delivering in the 14-day free trial. I noted that the average was 4-5 intros for that time period.

So I decided to deflate that number a bit when it came to setting expectations. On our trial onboarding call – coined “Account Optimization Call” – I'd tell our new trial customers, “You can expect to get 2-3 intros during your fourteen day free trial with us.”

Boom! Our narrative for success was set. And it ended up working out beautifully. About 60% of our trial users converted to paid customers. Perhaps the part of our sales funnel I was most proud of.

You might ask, “Paul, what about this success narrative made it so potent?”

Great question.

A few elements are at play here. The first? Our success narrative was anchored to an objective metric that's tied to value derivation from our product. There's no arguing with a metric. As a matter of fact, when folks would reach out mid-trial complaining about their lack of intros, I'd check their account. When they'd been doing well objectively, I'd respond, “You guys are seven days into your trial and already have 3 intros. That's a lot more than most. You've gotten the number of intros we'd expect for the entire trial! Candidates are responding super well to you guys. You're a sexy company.” This helpful reframe would most often get the trial customer to calm down and rethink how they'd initially perceived their experience.

The second attribute of our narrative that made it potent? Folks were conditioned pre-trial to expect these “aha” moments of value. Just like Pavlov's dog. There was an understanding that they were supposed to look for these intros. And once one was offered up, they'd think, ‘I'm getting to meet with this candidate I'd been interested in. This is cool. I wouldn't have been able to do that were it not for Whitetruffle.’ Value that was promised was delivered. Nothing like meeting expectations to build trust.

The third dimension of our narrative that made it powerful: we deflated our numbers a bit to make sure we cleared our bar more often than not. It was a layup for us to get there. As opposed to a three pointer. Or a stretch goal. By artificially picking a smaller number, we gave ourselves a greater chance at success. And nobody budged. Because they knew they were still getting three distinct moments of value.

So next time you're constructing a free trial or pilot, control the sale by setting the narrative for success for your customer. Don't ask them to formulate one. If you can make it based on objective metrics that are tied to value derivation for your product, that's even better. Plant the seed in your customer's heads that they'll be getting value every time this event happens. And lastly, deflate your numbers a bit, so they're attainable most often. I don't know about you, but I'd rather bet on a layup than on a three pointer.

Do all those things and you'll not only set your customers up for success. But also yourself. And if you ever want me to take a look at what you've concocted narrative-wise, just reach out to me at paul@gassee.com. Good luck.

Next week, we'll discuss how startup operators put too much pressure on themselves when personalizing their outbound.

Over the last 9 plus years, hundreds of founders have come to me for coaching on their sales and go-to-market challenges. And I've done my best to help. In the next few months, in the form of weekly episodes, we'll be looking at the top startup sales misconceptions folks possess. And how I get them to think instead. Reading this series will make you smarter and more aware than most startup operators, as you'll already know how to think about go-to-market and sales, and avoid some of the biggest pitfalls. Consider this your cheat sheet in shaving months off your revenue growth journey. Here's your fifth installment. Read on.

“I need my product and website to be ready in order to get started with GTM.”

“Paul, we want to make sure our website looks great and is optimized before we launch, and start reaching out to potential customers. Without it, we won't be putting our best foot forward. Folks might not understand what we do without it. And they might not be able to book as many demos through our site if it comes to that.”

Or I'll also get, “Our product needs to be full featured before we actually can get it in front of customers. Without it, I'm concerned we might be able to sell it when we get into conversations with potential customers.”

Hey, I get it. We all want to look and feel our best when presenting ourselves to the world. There's nothing like showing up to a date with lettuce in your teeth. Or to a job interview with toilet paper stuck to your dress shoe. Not great looks.

But in the quest for product-market fit, market interactions are actually more valuable than acting precious about our appearance or offering. And the sooner you start getting those reps, the better off you'll be.

You know why?

Because it's impossible to build a great product or website without market feedback. The perfectionism that's preventing you from going to market is also preventing you from perfecting them. Not only a mouthful. But a mind f*ck.

I can't tell you how much the above belief hurts startups. It's insidious. And becomes a preferred excuse for not exposing oneself to the market. Not letting the rubber meet the road.

And I get it. Doing all that takes vulnerability.

‘What if I discover that my product is lacking once I get to market? What if my website doesn't convert the way I thought it would?’

Let me help you with a reframe. Start with the premise that they'll both certainly fall short. That'll hopefully prevent you from experiencing any further disappointment. It's what Reid Hoffman was trying to help us with when he said, “If you are not embarrassed by the first version of your product, you’ve launched too late.”

You've got to realize this: once you raise a round, as a startup, you're sitting on a ticking time-bomb. Meaning, you've got a finite, limited runway until your startup goes ‘poof’. The earlier you get started with go-to-market, the more time you give yourself a chance to find message-market fit. Which is the discipline of figuring out what message you can put in front of prospects, that will garner their interest and have them wanting to have an introductory conversation with you. The more time you give yourself to figure it out, the likelier your startup survives.

Message-market fit is also part of product-market fit. And usually a scalable lever for revenue growth. If you unlock PMF at the seed stage, you've got your Series A raised quite easily.

Finding product-market fit will not only take getting your product in front of potential customers, but also getting it sold. Without getting the at-bats of getting in front of customers, it's impossible to figure out how to sell your product repeatedly. Or what things might be lacking in your product that need to be added in or changed. Every interaction or rep you get with the market, when properly analyzed, enables you to iterate, and get closer to product-market fit. And getting these reps – yes, you've guessed it – relies on you being in market.

You might ask, "How am I supposed to do GTM, if my product is not ready to actually sell, Paul? And how about my website? What if my positioning is not right? And prospects don't get the right idea about what we do once we've reached out and they then head to our website?"

Those are great questions. Your product doesn't need to be ready. First of all, finding message-market fit can take many months. I've seen startups take 6, 9 or 12 months to get there. Which means that you might not get an opportunity to sell to prospects until you get there. Also, one of the healthiest things you can do for your startup is de-risk it by pre-selling your product to them. If a prospect is willing to throw money at you to fix their problem, before you have a sellable product, and you're able to find several of these customers, that means you've found intense pain in the market, and validation that folks need your solution yesterday.

Yes, you'll feel the anxiety of having to fulfill your promise. But believe it or not, it's healthy anxiety. It's engaging in what some call 'market-led product development'. You're attentive to the market. Letting it tell you what it wants. And allowing it to lead you in the right direction.

As opposed to building in isolation. Which can lead you to catastrophic outcomes. There's nothing quite like coding away in our product caves for six to twelve months, only to realize that nobody wants what we've built once we re-emerge into the market.

As for your website, there's a lot that can be learned from go-to-market interactions that will make your website better. Sticking your neck out there, and listening to the market will allow you to figure out what value props and pain points you should be leading with in your website messaging, for example.

You might come to a realization like this one, ‘Man, I really thought CFOs were going to be excited about our software's ability to turn around reports in no time. Versus the hours their teams used to spend. But after speaking with a dozen of them, it's starting to feel like they care more about their ability to make better decisions thanks to the critical data we make available to them in real-time.’

The overarching lesson here is that you don't need to have things dialed in to get into the market. Lean into your humility. Adopt a growth mindset. Think of yourself, your product and your website as works in progress. And just let it rip! You can thank me when you start learning valuable things from the market.

Next week, we'll look at why it can be dangerous to ask customers what they'd like to accomplish in a free trial or pilot.

Over the last 9 plus years, hundreds of founders have come to me for coaching on their sales and go-to-market challenges. And I've done my best to help. In the next few months, in the form of weekly episodes, we'll be looking at the top startup sales misconceptions folks possess. And how I get them to think instead. Reading this series will make you smarter and more aware than most startup operators, as you'll already know how to think about go-to-market and sales, and avoid some of the biggest pitfalls. Consider this your cheat sheet in shaving months off your revenue growth journey. Here's your fourth installment. Read on.

“My product will sell itself once I demo it.”

I've seen this belief permeate Startup Land. "We'll just book a lot of demos, show our product off to prospects and then ask them to sign on with us. Done deal!"

That's just not how sales works. Or sales processes for that matter.

Flash back to early 2014. At Whitetruffle, we had just overhauled our business model; transitioning from a contingency fee-based shop to a SaaS company. My close friend & CEO Alex had handed me the keys of the customer-facing side of the business. And I was tasked with figuring out how we'd build our new sales model. I went to Mike, one of our cofounders, for advice. “Paul, I don't think we'll have a big enterprise motion here. You might not even need to demo the product.” Mike is a mover and shaker in The Valley, as founding partner over at Riviera. I had never designed a sales process from scratch. Armed with a 14-day credit card activated free trial, I aimed to keep things simple.

We installed a 15-minute qualification call with new prospects. After qualifying them, and getting them excited about our product, I’d tell folks, “Sounds like there's a fit here. Why don't we get you started with a 14-day free trial? It’s credit card activated, so you're going to have to enter your credit card. We'll be monitoring your account. If anything pops up, we'll reach out to address it together. And if any issues arise on your end, please feel free to reach out. We're always happy to help.”

Click. Prospects left the call excited at the possibility of testing out our tech talent sourcing platform. I could hear it in their voices.

And yet, guess what ended up happening?

Of all the folks that had both been qualified and committed to trialing Whitetruffle, only about a third of them would actually create trial accounts.

I couldn't believe it.

These folks had expressed their pain to me on our qualification calls. They needed our software to help them source candidates, so they could build out their tech teams. And yet two thirds of them weren't following through.

‘What the hell is going on? They want our product. Why aren't they starting free trials?’ I kept asking myself. Dumbfounded, I banged my head against the wall for weeks.

Then, a solution came to me. Mostly out of frustration. ‘If these folks aren't going to start these trials, we'll install a forcing function to make them do so’, I thought to myself. With that, we installed a trial onboarding call. Dubbed “Account Optimization Call”, it sounded a bit fancier and more value-laden. We sold it to prospects as a way for us to “ensure that you'll be onboarded properly to our platform and make the most of your 14-day free trial and beyond.”

Overnight, everything changed.

We went from having only around 33% of our qualified prospects converting to a free trial to nearly 100%. Interestingly, about a third of prospects would now show up to this account optimization call a little frazzled, apologizing for not having entered their credit card info and starting their free trial. I'd tell them, “No worries whatsoever. We're scheduled for thirty minutes today. That's more than enough time. If you have to go get your CFO's credit card right now, no problem. You can also enter yours. And swap it out later if need be.”

We finally had our backstop to get prospects doing what we needed them to do. The hemorrhaging of opportunities had stopped. And our sales were off and running.

A hard realization was also sinking in: human beings don't do what they're supposed to do.

Yes, as a salesperson, you might be within a prospect's top five priorities while they're on a call with you. Family, Faith, Friends, in whatever order they might have them. Then perhaps you: the seller. After all, you've got their undivided attention. But when the “End” Zoom button is pressed, you're likely to slide down that list. Fast. Their dog gets a case of indigestion and needs to be taken to the vet. Their kids come home with a project that needs to be completed by the next morning. Only twenty four hours later, you've likely slipped all the way down to number 19 on their priority list. Unintentionally. Without installing forcing functions to control the sale, you run the risk of deals stalling or dying outright.

Back to our original premise. Sales don't get generated just through demoing. Yes, a product demo can be an integral part of a sales process. But we build sales processes to take our prospects through a journey that maximizes our chances of closing them. We also need to do things like qualifying, conducting discovery, obtaining the buyer journey, sharing commercials, and obtaining a verbal close. These sales fundamentals are all part of controlling the customer conversation.

Building a successful sales process takes experience, intelligence, curiosity, and humility. After putting together the initial version, you're going to want to battle test it and refine it based on the feedback you're getting from the market.

And between these steps in the sales process, you're going to need some connective tissue. The reason why our Account Optimization Call was such a hit is because we made it feel valuable to the prospect. We sold them the next step. And with that, they not only agreed to get it scheduled, but they showed up in large numbers. It's not enough to build and refine a sturdy sales process, you've got to work on the transitions between stages. Those that know me in a sales context know how much I preach for selling next steps. Without it, you run the risk of massive leakage in your funnel.

Exhibit A. Our first sales hire at Whitetruffle was Chris. A student of the game (I knew I'd recruited the right person when “Fitz” handed me a copy of Challenger Sale in his first few days on the job. A book I devoured over a long weekend). The man is conscientious. After onboarding him as best I could onto our newly minted sales motion, Chris got in front of customers. A few weeks in, Chris astutely came to me with an issue: massive drop-off in his funnel post-intro call. Folks were willing to schedule the Account Optimization Call, but he was getting a lot of no-shows. As I listened to the way Chris was selling the next step at the end of the intro call, it didn't take long to unearth the root cause.

Chris wasn't yet fully articulating the value contained in our account optimization call. When prospects were seeing it pop up on their calendars, they probably couldn't recall there being something in it for them in the upcoming meeting. And thus would not attend. After a bit of coaching – the guy is a quick study – Fitz became assertive in conveying why it was in the prospect's best interest to attend our trial onboarding. His show rates rose up fast to above 90%. And his sales funnel was now patched up and humming on all cylinders.

The moral of the story?

It's great to have a well-designed sales process. But without sturdy connective tissue between its steps, you're running the risk of draining your pipeline of deals.

So next time you hear a founder tell you they're “just going to schedule loads of demos with our ICP, showcase our cool new AI product, and have them sign up with us right away.”

You'll know to say, “Hold your horses, Cowboy. How's your sales process? How are you going to control the sale? To make sure prospects stay engaged and on tracks to becoming a paying customer?”

Next week, we'll examine why it's rarely too early to kickstart your go-to-market.

Over the last 9 plus years, hundreds of founders have come to me for coaching on their sales and go-to-market challenges. And I've done my best to help. In the next few months, in the form of weekly episodes, we'll be looking at the top startup sales misconceptions folks possess. And how I get them to think instead. Reading this series will make you smarter and more aware than most startup operators, as you'll already know how to think about go-to-market and sales, and avoid some of the biggest pitfalls. Consider this your cheat sheet in shaving months off your revenue growth journey. Here's your third installment. Read on.

“I should give pricing when it's asked of me by the prospect.”

“Send me a quote, if you could. I'd love to review it with my team and then get back to you.” Prospects will ask.

And most junior reps or inexperienced startup operators will acquiesce. Although it's a huge mistake.

“But, Paul, don't we want to be customer-centric? Isn't it a good idea to give prospects what they want?”

“Of course, I want you to treat your customers with the greatest care. But not when you're doing yourself and them a disservice in the process.”

Let me explain.

When you send a quote to a prospect without having a chance to present it first, you prevent yourself from defending your offering's value, answer questions that might come up and even surface and handle objections. All things that are essential to closing deals.

Instead, when prospects receive a proposal, they'll often flip to the last page, to get to the commercials. And if your pricing doesn't fall within their budget, they'll let you know they're passing via email. Or they might ghost you outright. In either case, you don't get an opportunity to garner feedback as to why they passed. At the very least. And at most, you don't get a shot to do all the things that can lead to closing a customer. Including pulling a discount out of your backpocket, if need be.

“But, Paul, this feels manipulative. I hate when folks don't get me pricing upfront. Do I really need to wait until we get to a proposal review call?”

And I see where you're coming from. Does it feel more transparent to give everyone pricing at the very beginning?

Of course. But there's a strong reason why seasoned salespeople don't give pricing till much later on.

The longer you spend with a prospect, the more value you'll convey. And the more trust you'll build. Both ingredients to securing a paid customer.

If you give pricing at the very top of the sales process, there's a great chance your prospect isn't fully aware of the value of your product or service. And thus, comparing it to your (high) price will have them back away with sticker shock.

On the other hand, if you're able to give yourself the time to properly build up trust and the value of your product in your prospect's mind before presenting pricing, you're far more likely to convert as a customer. The value is so clear to them by then. It now feels like they'll derive value in the multiples of what you're about to charge them. And you've positioned yourself as their trusted advisor. Signing on the dotted line becomes the obvious choice.

Think back to the last time you purchased a complex product. Perhaps you'd been pulling your hair out about your accounting department's current processes. Specifically, you hate that it takes you hours upon hours to get an accurate picture of your account receivables. You'd love to be able to feel good about collections on invoices that have been sent out in the past ninety days. You end up reaching out to EasyAccounting, a mature startup you'd heard of from a buddy of yours that also runs an accounting team. Over post-pickleball beers, you remember him saying, “Dude, call them…best thing I've done.. Has made my life ten times easier. I get these gorgeous reports every Monday morning. I forward them to my CFO. And voilà…he's off my back now…I couldn't be happier.”

After filling out the inbound lead form, you're booked for an intro call with a sales rep named Tony.

“Hey Tony, great to meet you…got a great recommendation from my friend Greg. Can you tell me a bit about you guys…?”

Tony gives you a snappy overview of what his software can do, including the company's long-term vision. He qualifies you with a few questions and gets you talking about your pain in figuring out how to get a grasp on your account receivables. “Tony…I need to have an accurate, up-to-date picture of our ARs. But right now, it's cobbled together. With what-feels-like duct tape.”

Now, imagine for a second that Tony was to present you with pricing right then. After he got you to confess to your pain, but before giving you a slick product demo.

“Well, we typically charge $12K per year for our software. What do you say? Ready to move forward…?”

Not only would this feel abrupt and misplaced. But you'd have a hard time parting with that cash without also getting a sense for the savings you'd get from signing on. Do you fully appreciate the product's value at this point?

Likely not. You were just starting to get exposed to it.

Now let's envision this alternate scenario. Tony is able to not only wow you with a custom demo, but also take you through a rigorous ROI calculation. “With our software, customers typically save 10 man hours per accountant each month reporting on their account receivables. At $50/hour, with a team of your size, that's $8,000 a month. At our standard pricing of $12K per year, you'd only be spending the equivalent of $1K/month to unlock that saving.”

The fog has parted. And it's now crystal clear what you're getting for your money. An 8X return on investment. You're eager to transact. “I'll tell you what Tony, let's get this done…when can you onboard us?”

Let's consider the difference between these two situations. In one, you're given pricing without fully understanding what you're getting in return. In the other, the value has been served up to you on a silver platter, before the price was unveiled. If you don't understand what you're being offered early on, I'm likely to be scared off by a high price tag.

Yes, it might feel calculating to not provide pricing early on. But here's a helpful reframe. If you truly believe that your prospect is better off with your product in their hands. And that they'll be deriving value in the multiples of what you'll be charging them. Then, holding out on the price till later is just giving them a greater chance to benefit from your product and its stellar ROI.

Next week, we'll look into why forcing functions are critical to a successful sales process.