Uplevel had several viable paths forward. I interviewed Lauren Lang (who is a good friend) about how her team ultimately decided on a hybrid software + consulting model as the path forward.

This conversation has been lightly edited for length and clarity.

Brooks: In the simplest possible terms, how would you describe Uplevel’s positioning today?

Lauren: We have several little taglines we use, but one I keep falling back on is the operating system for engineering transformation.

And by engineering transformation, we mean adapting to this agentic AI-first software development lifecycle and completely changing the way engineering delivers value in an organization. It’s a huge technical, cultural and social shift all at the same time.

Previously, in the engineering intelligence space, there was this idea that enough data in a single pane of glass would unlock the magic of transformation. But when you’re adapting to new technology, it’s as much of a social and cultural challenge as it is a technical challenge. A dashboard might tell you that your developers are sitting in meetings all day, but not why…or what you could do about it. There’s a wealth of context that isn’t showing up.

So when I say “operating system,” I mean data, context and a playbook. When X happens, here are some of the possible root causes and some of the solutions you might want to consider.

In this space, it has become clear that not every problem can be solved by software alone.

Headline cred: Lauren’s mighty pen!

Brooks: What was the trigger? What changed where you said, “We need to reposition in the market”?

Lauren: We kept hearing from customers and now we hear this from prospects working with our competitors. “Cool, I see this data. What do I do now?”

We were having trouble writing case studies, to be honest. It was like, “We found a bunch of problems, but couldn’t fix them, so the numbers didn’t move.” Then I’m sitting there writing, “There’s so much more visibility.” Okay, so you have a front-row seat to what isn’t working, but you can’t change it.

The second trigger was AI. Companies thought maximum adoption would make productivity skyrocket because this was a technical problem, right??? But AI accelerated code generation, not the entire software development lifecycle. The bigger bottlenecks are around CI/CD and what happens before code generation…product management, requirements and clarity of direction.

Brooks: What were the viable paths forward?

Lauren: Viable path 1 was to give people what they were asking for, which was more granular AI data around token spend, adoption, code quality and acceptance.

That was viable, but it was also becoming commoditized. Find the data sources, connect them and there you go. It still doesn’t solve the underlying problem of, “Okay, what do we do?”

Viable path 2 was qualitative developer-experience data and surveys. But a competitor with incredible brand credibility had already cornered that market. Playing a me-too game on its own didn’t seem like a path we were going to win. And again, it was still better diagnosis. It wasn’t getting at the actual driving of change.

Brooks: Can I pause you for a second? You mentioned commoditization. Were you assessing which path would create more defensible value?

Lauren: Yes, but there were more paths.

Viable path 3 was to become a boutique consulting agency. So double down on transformation and change management and deprioritize the software. But data was still important for driving transformation and tracking progress. Also, we’re a team of engineers. We wanted to keep building things.

That led us to the Viable path 4…a hybrid solution that combines software and consulting.

The secret is leaning into engineering leaders’ preference for software and data. That’s the candy they want. Consulting is the broccoli they don’t want, but need so they can grow up big and strong.

Brooks: I love that language. So all 4 paths are on the table. How did you choose?

Lauren: This was a fundamental business-model decision, and it took a while – probably a good year. There were a lot of user interviews.

There was actually a Viable path 5 too: keep doing what we were doing and use AI in the product to make recommendations. That was tempting. We spent a couple of months testing different solutions with engineering leaders.

But ultimately, it came down to: “I don’t trust these recommendations. My organization is unique. Your platform doesn’t have the context I have, and I don’t have the context my teams have. So I don’t trust your data.”

There was fundamentally a trust gap. That told us we needed to get deeper with customers. There had to be a consulting motion if we actually wanted to drive change.

It really was a process of elimination. Consulting-only meant moving away from software. The survey market had been cornered. And with commoditization, we could see the end. The hybrid model was the only defensible path.

Brooks: So there’s the information side (interviews, experiments & customer feedback). Then there’s the internal alignment side. How aligned were you when you moved forward to messaging the new positioning?

Lauren: We have champions for consulting and champions for software. You build and iterate until you run into resistance, and then it’s, “Okay, we need to talk through this.” There’s always this negotiation around who we are as a company. How much is software? How much is services?

Brooks: But you got enough sign-off to execute. How did you bring it to market?

Lauren: We did an offer-design sprint first. We had software built for an old way of working, but none of the new consulting value was something we could demo. With skeptical engineering leaders who don’t like being sold to, we needed a different way to bring this to market.

So we designed a 3-phase GTM motion. The first step is a quick assessment. An engineering leader answers eight to 10 questions about their organization, AI maturity and how their teams work. We turn that into a profile, and they get on a call with a consultant.

It’s not a sales conversation. It’s a consulting session.

Brooks: And it’s free?

Lauren: Totally free. We’re going to give you a ton of value because that’s what we can do at this point. It lets us show our point of view and show that software alone probably isn’t going to deliver the value they need.

The second step is a paid 45-day transformation sprint called GearUp. We don’t begin by integrating all of their data because procurement and security slow down time to value. Instead, they spend about 45 minutes sending us reports. We interview developers and managers and survey the team.

Then we hold working sessions and ask questions like: “Does this data feel right? What are the real problems? What might work for your team?” The teams become part of the recommendations. By the end, they’re implementing changes, and we can provide the business case for the larger transformation.

That third phase is our core product: a typically multi-year engagement combining software integration and transformation consulting.

Brooks: What are the early signals? Is it working?

Lauren: We’re still optimizing that first step. We initially positioned it as, “Can your system even handle an AI transformation right now?” It became an AI-maturity assessment, and that terminology is very saturated. From an inbound standpoint, we’re still figuring out how to phrase it in a way that feels differentiated.

But it has worked very well in founder-led outreach.

Our CEO can say, “Come to this first call and we’re going to tell you something you didn’t know about your organization.”

We’re seeing more pipeline generated from that.

Brooks: The free consulting feels like part of the positioning too. You’re giving away the frameworks and thinking upfront.

Lauren: It is part of the positioning. They don’t trust us yet. They need to know why they should listen to us and that we have a very different point of view in this market.

We are not the tool you come to when you want to optimize token spend. That is not what we’re here for.

We’re also not going to lead the AI hype cycle. We have a more measured, practitioner-focused approach. We’re not the new hotness, and we have to be okay with that.

I think we’ll be the company people come to after the fancy dashboard didn’t work or token-maxxing ran out of money. We’re going to be on the tail end of the bell curve.

Brooks: Is the buying trigger basically, “We tried the AI-transformation thing and it didn’t work”?

The transformation isn’t really about AI. It’s about building the capability to learn and adapt, and then respond to disruption, the market and customers. Team structures and org design are changing, and the work depends on feedback loops, technical foundations and CI/CD.

All of that should have been in place before. It turns out it was load-bearing when AI entered the picture.

So our plan is to keep working, be patient, be persistent, and keep banging the same drum that “Your easy button is not going to work.”

Here are the details:

• Here is 17-minute recorded example of me doing the diagnostic audit process on myself so you can see what it looks like.

• You must be 1) a founder or 2) a marketing leader at a growing B2B company or startup (no consultants, freelancers or prototype-stage founders sorry)

• We’ll hop on a call, open up a Google Doc & work through this exact document together. I’ll share my screen and write everything out live as I grill you with questions. That same day, I’ll send you the completed document and Google Meet transcript so you have a clear read on where you are in terms of positioning.

• I do ask that you 1) spend 10 mins reading this slide deck beforehand. That way, you’ll understand how I think and we can hit the ground running as soon as the call starts.

• This is not simply a pitch for my services.

• The audit is entirely dependent on your knowledge and data. I don’t know your company, product or customers like you do.

• This is a quick shot of positioning espresso (the 5 bean option). There’s almost no preamble so come ready for rapid fire questions.

If you’re a fit (or know someone who might be) here’s the link to book:

https://calendly.com/brooks-brookslockett/positioning-audit

To win a real market, you need 3 things:

1) honesty

2) decisions

3) repeatability

Let’s look at how to know if you’re actually ready to build a fortress, or if the concrete is still too wet to stand on...

Most of my days are spent with growth-stage B2B companies, but occasionally I get into the mud with early-stage startups.

Across all of these projects, one high-stakes lesson keeps popping it’s head up…

You must know the difference between a positioning thesis (a hypothesis) and a validated market position (a proven reality).

Think of a position as “land” in your prospect’s brain that you had to fight a war for.

Once you’ve bled enough to earn that territory, it is incredibly difficult for a competitor to kick you out.

Human beings HATE changing their made-up minds. That’s positioning 101 (straight from Madison Avenue in the 1980s) and it’s still the absolute truth.

But how do you know if you’re actually ready to claim your land?

If you can answer these six questions with 2–3 market-tested points (instead of a brainstormed laundry list of 15 guesses), you are ready:

1. What alternatives are we replacing?

   1. (How are they getting the job done today?)

2. Which advantages can we credibly own?

   1. (What is our actual differentiator?)

3. Why do those advantages matter to our buyer?

   1. (What is the “so what?”)

4. Which proof points do we have to back it up?

   1. (What is our evidence?)

5. Who are our best-fit buyers, and why do they need to act now?

   1. (Who is suffering the highest cost of inaction?)

6. Which market category do we belong in?

   1. (Where does our prospect’s brain naturally file us?)

To find out if your positioning is real, ask yourself with brutal honesty…

How fluid is my situation?

• Do the answers to these questions change depending on the week?

• Does your target market depend on who you chatted with yesterday?

• How confident are you that these answers won’t shift by next Monday?

• Do you have quantitative data to make these calls?

It’s not always black & white.

Maybe you are 100% clear on your best-fit buyers and capability mix, but you’re using the wrong market category framing. Or maybe you tried to invent a brand-new category and realized it’s too abstract to help anyone actually buy.

If your answers are constantly shifting, it is simply too early.

The logic is…to win the war for that space in your prospect’s brain, you must repeat your message consistently for a long time. To repeat it, you have to actively decide to stick to it.

The paradox of early-stage growth is that B2B markets are flooded with tempting opportunities. If you just “listen to customers” without a guiding theory (ahem... positioning), you will get chaotic data that pulls your product in ten different directions.

If this sounds fucking hard, it’s because it is.

But it’s also the exact thing that separates durable brands from temporary, commoditized “me-toos”.

Timing is everything.

Every company needs positioning... but not always right now. You cannot make strategic decisions you can stick to while your foundations are still fluid.

Since you’re on an email list called B2B Positioning you’re likely staring down this exact crossroad.

Are you ready to claim your land today, or do you need to give it a little more time?

Your homework is to talk to your prospects with this lens.

Record your customer discovery calls, run them through an AI analyzer, and pull out the exact vocabulary of your buyers.

It is far better to ruthlessly pressure-test your positioning today than to launch a product based on flawed assumptions. I have made this mistake myself, and I can tell you that rebuilding a broken product-market fit is brutal.

When you secure a foundation you can actually stick to, your messaging aligns effortlessly.

You stop arguing about adjectives because you’ve already made the “meta-decisions” and documented the exact data that justifies them.

But if you are in the super-early stages, you just need more of this:

Your positioning pal,

~Brooks

It’s a suspiciously simple idea.

Doing positioning work with a company is another matter.

I have tremendous, tremendous, tremendous respect for founders.

They start with nothing, build products, hire people & then make serious investments in growth (usually while absorbing levels of risk and uncertainty that would make most people deeply uncomfortable).

And for years, almost every sign of progress involves adding something (features, buyer segments, use cases, possibilities).

Then a positioning consultant comes along and asks, “Okay, but what matters most?”

Or worse: “What are you willing to leave out?”

This is where an idea that sounded perfectly reasonable in theory becomes much harder in practice.

Pro tip: always deliver this perspective in a tasteful, respectful, context-aware manner. You run the risk of being the punching bag if you’re telling people to kill things they’ve built that are not serving them.

I recently wrote about a founder I worked with years ago who thought positioning meant adding an adjective.

He went line by line through our product copy and told us to “position” each feature as “THE BEST”.

It’s funny now, but it’s also a perfect example of confusing the task with the work. He was changing words without making any of the decisions underneath them.

But that’s also what makes positioning difficult.

Every company should do it. Not every company is ready to live with the decisions it requires.

Early on in a project, I walk clients through a deck I call The 6 Positioning Decisions.

I made it intentionally simple.

6 decisions & 1 place to annotate/track them.

For each one, we ask:

• Do we have enough information?

• Are the right people aligned?

• Have we actually decided?

In a perfect world, every decision ends with three green stamps:

Reality is usually messier.

There are a lot of people on this email list who write copy (including me!).

Some for clients, some in-house & some as founders.

So here’s a useful question:

Have you actually reached “high information, high alignment, decided” on every positioning decision required to tell the story over and over again…enough to acquire that precious mental real estate in the mind of your buyer?

Probably not (almost nobody has).

That doesn’t mean the work stops until perfect alignment descends from the heavens.

In fact, copywriting is often where you discover whether the decisions were real.

I’ll leave you with this.

> Everyone worries about differentiation

> But most companies never reach this level of decision clarity

> If your company can make & stick to clear choices

> That alone will make you unusually different

My service carries positioning decisions through to the bottom of the funnel, where they become websites, sales decks, landing pages & sales emails.

But that isn’t where the work ends…it never ends :)

Still, you have to start somewhere.

And when the darlings inevitably return, remember what you decided.

Talk to you next week.

~Brooks

And that superpower is becoming much more valuable because AI has made adding more ideas effortless.

MORE MOOREE MOOOREEE MOOOOOOORRRRRREEEEEEE!

And guess what? Buyers tune most of it out.

Back in 2024, Sam Altman said OpenAI was already generating about 100 billion words every day.

I don’t need to remind anyone how much more at-scale AI is 2 years later.

The buyer’s brain has not expanded to accommodate all of this.

It’s just getting hit with more.

April Dunford recently expressed the point beautifully:

I commented that it disappoints me that the late positioning old timers aren’t around to see their prediction become truer by the year.

Ries and Trout first published Positioning: The Battle for Your Mind in 1981.

The 2nd chapter was called:

They wrote about an overcommunicated society where companies were already struggling to reach overwhelmed buyers.

That was in 1981.

I wasn’t even born yet.

MTV launched that summer, and the first video it played was “Video Killed the Radio Star” which feels almost too perfect.

None of these are new problems.

But FUCK have they gotten worse.

In my client work, the first step is taking a full inventory of everything that already exists (and this is where things have changed a lot since ~2023).

Even teams of 1 or 2 people now have so much stuff.

Landing pages + old positioning docs + too many feature pages + random email sequences + sales 1-pagers + a million other half finished ideas.

I’m not saying they’re directionless, but they definitely are overbuilt.

To borrow from Arnie:

What I end up doing in positioning work is pruning an English garden that’s been allowed to grow 100x beyond its intended shape, and turning it into a French garden.

It’s good ol’ fashioned discipline.

A big part of this work is to decide what the company stops spending time on entirely (which is an uncomfortable yet extremely productive conversation for clients).

I’ll be sharing some client examples of this in future newsletters.

But if I leave you with one net learning, it’s that subtraction is hard…but subtraction is positioning.

Take another look at your product or service, and ask yourself:

1. Is it genuinely too complicated to explain simply?

2. Or have you avoided deciding what matters most?

Give buyers the radical simplicity they’ve craved since 1981, and they’ll show you with their dollars how much they love you for it.

~Brooks

Totally fair!

The last time I was writing here (2024), I was sending daily emails about AI.

And at the time I was genuinely excited about it (still am).

But behind the scenes, things were chaotic.

Over the past few years I was doing a lot of different things at once (consulting work, writing about AI, trying to figure out where I fit in that whole ecosystem).

Then in early 2025 I joined an AI startup full-time.

From the outside, it probably looked like momentum. There were lots of congratulations and “happy for you!” messages.

Inside my own head, it felt like the opposite.

I was constantly busy, but not moving in a direction that felt coherent.

In October 2025 I left that company.

And for the first time in awhile I gave myself space to slow down and actually think.

Since then I’ve mostly been in what I’d call “the lab” doing a look back at the work I loved doing the most that solved the hardest problems.

A pretty clear pattern started to emerge…positioning.

So that’s what I’ve decided to focus on…completely.

I relaunched my consulting website entirely around that work and what I’m building going forward.

If that’s interesting to you, I’m glad you’re here.

If not, completely fair. Feel free to unsubscribe.

Either way, I appreciate you being on this list.

From here, I’ll be writing about how B2B and AI startups are making positioning decisions as AI reshapes their markets, categories get more crowded, and competitors become harder to tell apart.

Let’s see where this goes!!!

Brooks