(Don’t worry, not that kind of a bad idea.)

The whole interview process for this company had been strange. They didn’t really have a job for me. I met and interviewed with a whole host of people, and then they offered me a VP job, not on the executive team, with dual reporting lines.

It felt messy. Like there wasn’t really a role. I turned it down.

The CEO followed up and asked to continue the conversation to see if there was a better fit elsewhere. We met again and he drafted a job description. It sounded interesting.

He suggested I meet with his Chief Strategy Officer.

The Chief Strategy Officer emailed the morning of the interview to say he had a contractor coming and asked if we could meet on his patio.

This was 2021. We were used to meeting in odd places to avoid being inside with strangers. It seemed a bit weird, but my husband and I discussed and decided it was okay.

I biked over to his house. He met me outside, took my bike, and put it in the upright bike rack in his garage. He shut the garage door behind us as we walked around the house to his beautiful landscaped patio.

He offered a glass of water and we chatted about the neighborhood and the landscaping before diving into the interview.

He first asked what I was most proud of. I talked about my work at Owl Labs. Launching the product, running out of inventory, selling through that, and growing to generate $50M a year in revenue.

His next question, “Did you get worked out of Owl? Or fired?”

He drilled into the details of my departure, and then said, “I have asked around about you, and you have a reputation for breaking things. What do you think about that? You can defend yourself.”

I was taken aback and thought, That’s my reputation? According to who?

I pulled it together and said, “One of the things I have learned about myself is that I can steamroll people. I often get to the answer or the thing that needs to be done very quickly and in the past, have been very direct in telling people. I’ve hired myself an executive coach and learned how to meet people where they are and bring them along more effectively. But it’s possible, when people say I break things, they are talking about being very direct about the problems and sometimes overwhelming people.”

He acknowledged that was a good answer and then asked about my biggest failing.

I talked about joining a seed-stage company, even though I couldn’t make the product work when I tried it.

He told me it sounded like I had confidence problems.

Do I have confidence problems?

He challenged every answer I gave and refused to answer my questions.

He accused me of trying to insert myself into a leadership team that didn’t need or want me.

He told me he couldn’t recommend that I be hired. He said it would be too disruptive.

He offered me a job working for him instead.

He told me that members of the existing team were very angry with me.

I started to cry. (I hate that I started to cry.)

He offered me a hug.

Oh god, what the hell have I gotten myself into? How do I get out of this?

I couldn’t even leave. My bike was shut in his garage.

When I finally asked to leave, he helped me get my bike and we shook hands goodbye.

I was so shaken and upset, I couldn’t bike home. I walked and cried.

Once I got myself together, I called the CEO and said I was no longer interested in any role at the company. The conversation was short, 2-3 minutes. I didn’t feel the need to explain myself.

The next morning, I was worried about having a reputation for breaking things. I was between jobs and that felt like the end of my career.

I still don’t know where it came from, or if he made it up.

When I joined the company, there wasn’t a product team. Brian Halligan was directing the engineering team’s efforts himself. A few months after I joined, he realized this wasn’t sustainable.

I was on the customer success team, which was the job they were hiring for when I applied. I learned about the problems of the customers and about the tools we had. It was a great place to start.

I pretty quickly knew it wasn’t the job for me. I didn’t enjoy teaching people to use the software. I wanted to build the software.

When they opened up the Product Manager role, I was excited and applied immediately. As did another HubSpotter who had recently joined the customer support team.

When the decision was made, I didn’t get the job.

I was disappointed. Not getting the job meant more days spending hours on the phone, not building.

I decided to make some changes to get closer to building.

First, I moved my desk to sit with the engineering team.

Our office space was made of a collection of small rooms. Each room had 3-4 desks, and I was sitting in a room mostly alone. That was good for making customer calls, but not great for feeling connected to the team or to the work I was excited about.

I didn’t ask anyone; I just picked a new desk and moved. No one cared.

I also started attending the engineering team’s daily stand-ups. I was on the phone with customers 6 hours a day. I could share how they were actually struggling.

It only took a few weeks for leadership to realize that one product manager wasn’t enough. They needed to hire another.

It wasn’t a big leap from that decision to, “Karen’s already doing the job. Let’s move her into the role.”

The first PM they hired and I became the product team and worked together for the next 4 years. We’ve since worked together at another company and are still great friends.

I didn’t ask permission to make these changes. I just made them. Looking back, 18 years later, I am in awe of my own gumption. I wonder if I still have it.

For the second company in a row, I had missed the signals completely and landed in a place where the founders and I were fundamentally misaligned.

I went from thinking we were finally turning things around, to missing dinner with my kids on a Friday evening, as I had a heart-to-heart with the founders and realized we weren’t even close.

I resigned the following Wednesday.

I was in the middle of my second job search in two years and was beginning to wonder if what I was looking for didn’t actually exist.

I was searching for a partnership with founders who wanted what I bring to the table.

An investor who I knew through the Boston startup scene but had never worked with, gave me some critical advice.

He said, “The problem you’re making is that you keep working with first-time founders.”

He went on to explain that first-time founders are trying to prove themselves to the world.

They believe in order to be taken seriously, they need to know how to build the perfect product and the perfect go-to marketing strategy all while knowing how to manage a board and lead a team.

They often struggle to incorporate other leaders to help them.

The next day I narrowed my search down to companies with repeat founders, who had been successful before, and who were looking for an operational partner.

I talked to 2 companies.

Both were great opportunities with excellent founders.

I chose to come to Sense.

That was over 4 years ago and I am still here.

It’s not intentional.

It can happen when I am super excited about something, or when I am impatient and want to start moving. It can also happen when I am short on time, or when I don’t feel like I am being heard.

I first heard this from my executive coach. There were people and personalities I was struggling to navigate at work. After working together for about a year, I trusted her.

However, this was hard to hear, and I didn’t accept it right away. At first, I pushed back. It felt like gendered feedback.

“You wouldn’t be telling me this if I were a man.”

She assured me that she had given this feedback to men as well. And that yes, there are times and places where men are allowed to take up more space, but that doesn’t change the impact I am having on others.

When I struggled to figure out how to put her guidance to work, I pushed back and said,

“Why should I be the only one to change?”

She reminded me that everyone is on their own journey.

It took time, and working through different situations together, over years, for me to finally start to figure it out.

I now know that it doesn’t matter why I do it, or if the expectations are gendered, or if other people aren’t working on their own challenges.

The bottom line is that it never feels great to be run over by a train.

I have to meet people where they are. Not force them to always come to where I am.

Sometimes I have to slow myself way down and really focus on listening. Other times they are as excited as I am, and I can jump right in alongside them.

It still happens.

I am not perfect. I do work hard to pay more attention to how someone else is reacting in the moment. To ask more questions before I jump in with enthusiasm.

And, at the end of the day, what I love most is when things click with a person or a team and just feel right.

For that to happen, I have to do my part and slow down the train.

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Extensive testing in the bathroom mirror after the fact has me convinced no one noticed.

And it certainly distracted me for a bit during the meeting when I sat down and realized what had happened.

It’s not the first time I have had a wardrobe malfunction at work. (Please tell me I am not alone in this!)

The worst was in front of 200 HubSpot employees.

Every two weeks, we would demo what we were working on. I was the PM for two teams, the Red Sox and the Celtics. (This is Boston, of course, our scrum teams are named after sports teams!)

I would introduce myself. “Hi, I am Karen, the Product Manager for the Red Sox.” And then share what we had built during the last sprint.

Then I would jump in the air, spin around, and say, “Hi, I’m Karen, the Product Manager for the Celtics.” And share the second team’s work.

I was dressed up one day and wearing heels.

As I jumped into the air, I remember thinking that this could be a bad idea.

I was so focused on landing without breaking an ankle that I didn’t realize my skirt was lifting up over my head until it was too late.

Until everyone in the company saw my underwear.

I landed (and did not break my ankle), and everyone cracked up. I am certain I blushed. I probably made some crack. It’s all a blur.

Then I launched into the second presentation, which was arguably the more important message. I was sharing something the team really needed to know.

I did my best to pull it together and continue. I don’t think it went very well.

When I was done, I sat down next to Jeanne Hopkins so the other product managers could present.

Jeanne was a mother and the most experienced woman at HubSpot. I leaned over and asked her what color my underwear were.

She patted my legs and said, “They are tasteful black panties. Don’t worry about it.”

It was exactly what I needed to hear. And I didn’t listen to a single thing the other product managers presented that day.

Although I had put together a lengthy proposal, no one ever read it. Mike Volpe told me he had heard about the idea and suggested we record the first episode at 4 p.m. the next day.

I ran to Best Buy with one of our engineers and bought some microphones and a video camera. We figured out the rest in the hour before our first recording.

Four years, 225 episodes, and one Webby nomination later, we retired.

We started HubSpot TV in 2008, and it was the first business podcast of its time.

Mike and I would spend a few hours each week collecting stories to talk about and creating a rough script. Team members across the company helped us produce it. We built our early set out of orange bed sheets, PVC pipes, and MDF boards.

Every week at 4 p.m. on Friday, we would open the office to the community and host the show live in front of the audience. Most weeks, we would get 20-30 people who would come for the free beer, networking, and 20 minutes of marketing entertainment.

It was the very best kind of startup scrappy.

We talked about the marketing stories of the day and made jokes that were not always work-appropriate.

Mike was the steak, and I was the sizzle.

He was there to bring us home and remind us of the marketing lessons. I was there to keep it entertaining and slightly off-color.

I loved being a part of it and had a blast making the shows; it was also a lot of work that didn’t have anything to do with my actual job as a product manager.

More than once, I tried to shut it down.

In a company that lived or died on data, the success of the show was hard to measure. We didn’t have overwhelming viewership, and while it had a consistent live audience of 20-30 people, it never really grew beyond that.

HubSpot TV survived because every time Brian Halligan (the CEO) went somewhere, people would mention it to him. It helped to build the HubSpot brand, and as is often the case with brand marketing, the impact was felt more than measured.

Every time I brought up ending the show, Brian would suggest that instead, we go bigger. Occasionally, he would suggest that I become a full-time brand ambassador. Traveling to conferences, giving talks, spreading the word.

I always refused.

I not only loved to work with the engineering team building products, I was also very protective of my technical degree and skills. The idea of moving from a technical role where there were so few women to a marketing role where there were so many felt very typical and boring.

I knew if I left product management, it would be difficult, if not impossible, to return. And I wasn’t willing to do that.

While I was protecting my place on the product team and refusing to move into marketing, what I missed was the impact HubSpot TV had on how I was perceived outside the company.

While I never took on a full-time brand role, I did speak at conferences and built up an impressive following on Twitter. Within the Boston marketing and startup community, HubSpot TV and by extension, Mike and I, were well known.

The challenge with continuing to do both jobs didn’t show up until I had left HubSpot and was starting to look for my next opportunity.

It showed up in a way I had never imagined.

People only wanted to hire me as a marketer. I couldn’t get jobs leading product teams.

Regardless of how I had pushed to stay a product manager, HubSpot TV had branded me a marketer. It didn’t matter that I didn’t have the experience in marketing or that I did have the experience in product management.

I never realized that people outside of HubSpot wouldn’t see the hard work I was doing building products. They would only see the sizzle I brought to the podcast.

The good news is the HubSpot network is strong. I eventually landed at Quantopian with a group of ex-HubSpotters and was able to build incredibly technical products and speak about them publicly, rebuilding my external brand as a technical product person.

And although people say things on the internet last forever, they don’t. Most episodes of HubSpotTV have been lost to time, and it rarely comes up.

Occasionally, I run into someone who remembers, will connect me to the show, and say, “You’re THAT Karen Rubin?”

The first 15 years of my career were spent in product management, working with engineering teams, defining, building, and delivering products.

Until Owl Labs.

At Owl, I was hired to do everything that didn’t touch product or engineering. Things I had never done before. Sales, marketing, operations, and customer support.

I was hired for my potential.

I learned about the company from an investor I had worked with before. The company was in stealth mode, and he was considering making an investment.

He shared the deck with me.

I took one look at the product and wanted it to exist in the world.

I was working with an engineering team that was mostly in person, but every day at least one person was remote. For stand-ups, we would all stand in a circle in the office. As each person gave their update, I would hold my laptop in front of me so that the remote person could see and hear the people via Google Meet.

The Meeting Owl was the perfect solution to this problem.

I called the investor and told him I thought he should invest, and asked if I could get one of the video cameras to use in my office.

I also told him I’d be interested in a position. I believed in the product and wanted to help make it a reality.

He told me the cameras didn’t exist yet and that he would finish his diligence and be in touch.

A few weeks later, he called. He had made the investment and wanted to introduce me to the founders.

We spent some time together. I got to see the Owl in action, and was even more convinced.

There was only one problem. They didn’t need a head of product; the CEO was doing the job.

What they needed was someone to think about everything else so they could focus on delivering the product.

I pitched myself for the job.

I explained I could learn anything I needed to learn to figure it out. I hadn’t known quant finance before I started at Quantopian, or anything about marketing before I went to HubSpot.

The founders listened, and then the investor vouched for me. He believed in me and convinced them to as well.

The night before I started, it hit me. I was being hired like a man, for my potential.

In every other role, I had been hired for the things I had already done. It was rewarding and validating, in a backwards direction.

Getting hired for my potential pulled me forward. It was a vote of confidence that I could do something I had never done before.

I wrote this post after receiving a message asking me to share stories about how I transitioned from finance to product to GTM to operations. The jump from Quantopian to Owl was the biggest; it was the shift from 15 years in product to something completely different, and so here it is.

I love questions; if you are curious about something, please send it my way!

Many kids at Trinity College spent their entire college career working on landing a job as an investment banking analyst.

I was not one of them.

As I navigated my senior year, I didn’t even know what investment banking was. I had a degree in computer science and all I knew was that I did not want to be a programmer.

I had done one year of programming at a huge company. Sitting in a sea of cubicles, working on a project to develop a training database, I felt certain that programming was not for me.

The choices that the Trinity College career office was prepared to help you navigate were med school, law school, more school, investment banking, or IT consulting.

In the fall semester of my senior year, I wasn’t too worried about finding a job. I was mostly focused on running and figured I would look for work after the cross country (XC) season was over.

I was a 3-season athlete. Running XC in the fall, indoor track in the winter, and outdoor track in the spring.

I was the captain of the XC team, and our team placed 2nd at the National Championships that fall. We also had the highest GPA of any sports team at Trinity that season.

I was asked to come speak in front of a group of alumni donors. They asked me to share my experience at Nationals and help them understand why the women’s cross country team was both performing at a high level and achieving good grades in the classroom.

After I spoke, one of the alumni came up to me and said, “Hi, have you ever thought about working on Wall Street?”

I laughed in his face.

I explained that I was getting my degree in computer science. I was not one of those finance kids, and I was going to head into IT consulting after graduation.

He offered to bring me down to NY to show me what investment banking was all about.

A week or so later, I took the train from Hartford to Grand Central Station. It was my first time ever going to NYC on my own.

As I walked from the train station to Madison Square Park on a beautiful spring day, I imagined what life would be like living in New York City. I’d wear fancy clothing, get pedicures, walk to work, and pick up a cappuccino on the way. I’d work hard all day, and then get cocktails with my friends at fancy restaurants.

I had watched my fair share of Sex and the City, and was already sold.

I spent the day talking to analysts at Credit Suisse First Boston. They told me of working directly with CEOs of leading brands, and taking town cars around the city. They said I would work hard, but that I would learn an incredible amount about all aspects of business.

There were none of the famed panel interviews. I honestly don’t remember any interviews at all. It was a series of discussions, most aimed at answering my questions.

At the end of the day, the HR department offered me a job making more money than seemed reasonable for someone coming right out of college.

I thought about it for a week, then accepted.

I went home for Christmas with a job lined up and was ready to spend the spring of my senior year enjoying myself. When my ex-boyfriend from high school dropped off the book Liar’s Poker by Michael Lewis and suggested I read it, I threw it in the bookshelf and didn’t bother.

The following summer, I moved to New York to start my new job, ready for the hard work, the fancy clothing, the CEOs, the town cars, and cappuccinos.

Nine months later, I quit.

I had the responsibility of setting the strategy, creating the roadmap, and then making it all happen with the engineering leaders.

I love to build, so at first, this didn’t seem like a problem.

Until we started to build more products and I couldn’t keep up.

I was drowning in work. Dropping the ball on the newer products that needed more time for research, focusing on the things I already knew well and could trust the engineers to carry.

The story I was telling myself was that I was being taken advantage of. I could keep taking more on, and doing more, and it benefitted the company because they weren’t paying me more.

I was annoyed.

One day I finally went to the CEO and asked, “Why are you not letting me hire a team?”

His answer was very short.

“You didn’t ask.”

I sat there stunned.

I was supposed to ask? The thought hadn’t occurred to me. I assumed that “leadership” would have a hiring plan, that they would hand it down, and I would be granted people on my team.

It was the shock I needed to realize, I was now leadership.

It was my job to determine what the team needed to be successful and then to advocate to make that happen.

In hindsight it seems so obvious, and in startups, we rarely prepare people for the new responsibilities when they level up. We expect them to understand or to figure it out.

When I was promoted to director, I struggled to step outside of the day-to-day to-do list and find time to think about the bigger picture. I was comfortable getting shit done, and the big picture thinking was new and a bit uncomfortable.

So much learning has come when I have failed to do something that I didn’t realize was my job.

Like understanding it was my job to figure out that we needed to hire additional PMs and advocate to make it happen.

It wasn’t difficult to realize I needed to take a break. Figuring out how to actually take one took some work. As a driven, type A person, slowing down doesn’t come naturally for me.

I did what any sane person does, I made a list.

How would I normally spend my time? What things would rejuvenate me? What would not?

That helped me realize that I needed to keep my mind and body active, while also leaving plenty of flexibility to do whatever I wanted to do.

I made another list of things I had always wanted to do, but never had the time to do.

Making cheese. Learning statistics. Reading non-fiction books. Returning to yoga.

I then made a plan for time off and set off to relax. It sounds ridiculous. I realize that. And it worked. Eventually.

The first few days I couldn’t turn it off. Owl had been an intense learning opportunity. I was afraid that by stepping away, I would somehow lose hold of the lessons and it would become meaningless.

I decided to sit down and write. I made yet another list of all the topics I wanted to cover. Data. Passion. Transparency. Talent. Hardware.

I committed to one topic per day until they were done. The kids would leave for camp, and I would sit down and write. There wasn’t a purpose to my writing other than to get everything about that topic down on paper. Stories, frustrations, ideas, lessons.

I wasn’t writing to publish. I wasn’t aiming for a plot or structure. I was just aiming to get it out of my head and onto paper. Where it could rest until I was ready to pick it up again.

14 days later, I was free.

The lessons had been preserved. I was able to sit and relax. I never did get to cheese making, but I started yoga again. I took the statistics class I had never taken in college. I read a few non-fiction books.

A few months later, I was ready to get back to work.

Figuring out I needed a break wasn’t hard. Figuring out how to let go of all the things in my brain was harder. Writing gave me the room to just be for a little while. It was enough.

Claude helps me write my stories.

Before you throw eggs and unsubscribe, let me explain. (And trust me, this comes back to the stories I am not ready to tell.)

I have a Claude project that has been trained on everything I have written for Not a Straight Line. I’ve given it the specific instructions to make suggestions and to never rewrite my words unless I ask it to.

I write the first draft and ask Claude for feedback. It doesn’t change anything, it just tells me what isn’t working.

It’s a bit like getting feedback from Ms. Anselment, my 10th grade English teacher.

The difference is with Claude, I can choose which advice to listen to, and which to ignore.

The other day I took it a step further and decided to use Claude as a brainstorming partner.

It is important to me that I not just write about my successes. Not every company I have worked at has been a huge success. I have made bad choices and been a part of failures too.

And, I am very conscious of not pointing fingers, sounding defensive or complaining. I want to share my lessons, not the baggage.

I asked Claude if it had any advice for me on how to share these stories.

It asked for an example of a story I am hesitating to tell. I shared some details of a challenging relationship. An experience I learned a lot from, and haven’t written about.

Claude’s response,

“Some stories just can’t be told yet….Right now it sounds like you’re still holding on to some anger.”

It was exactly the right answer. And deep down, I already knew that.

This AI bot said the thing out loud that I wasn’t fully ready to admit to myself.

Claude isn’t writing for me. It is helping me find my voice and be honest with myself about which stories I am ready to tell.

The next day, I sat down and wrote a different story about another hard decision. It became my most recent post. It was a stronger story because it was one I was ready to tell, with more lessons and less baggage.

I was leaving a company I had joined 3 months earlier, and a venture capitalist I respected asked me that question.

I was confident in my decision to leave. However, I would be lying if that question didn’t give me a moment of doubt.

How could I possibly know after only 3 months?

I joined because I believed in the product and had seen the technology work. It was very early stage, and the company had just raised $20M from people I trusted.

I quickly connected with the team. I genuinely liked the people I was working with. They were smart and dedicated.

The problem was that there was no focus.

The technology did one thing, but the product was going to do that one thing….and 10 others as well.

The market we were targeting was…..basically everyone.

There wasn’t a use case that we weren’t going after.

In order to support the product and marketing explorations, we were hiring at an unbelievable rate. I was employee #13 and before I left, 3 months later, we hit 70 people.

I didn’t know our burn, but I knew that given our timeline to market, the hiring was unsustainable.

A friend who was at a different company and I went out to lunch. They were looking to hire someone and had come to me in the hopes of an introduction. I surprised us both and suggested myself.

What gave me the conviction to walk away? How did I know I would be on the right side of that question?

It wasn’t easy. I felt like I was abandoning new colleagues who were becoming friends. Building teams and relationships is what drives me, and walking away from that was the hardest part of the decision.

Ultimately, I realized that I needed more than great co-workers, and a problem that I believed in.

I needed to believe that the leadership team was steering us in the right direction. That they could make the hard decisions about what market to target, which use cases to focus on, and which employees we really needed to hire.

Once I was honest with myself and admitted I lacked faith in leadership, the decision to leave was easy.

Four years later, the company shut down, having never launched a product.

I was the person who saw the writing on the wall and learned that when things feel fundamentally wrong, I should listen.

At the age of 25, I was the Director of Content Solutions at a mid-sized media company in NYC. My clients were NBC, Hearst Media and TheStreet.com. I managed a team of 40 engineers, project managers, and designers.

It was a great job. I enjoyed my team and clients, and was learning a ton. And I decided to leave it for an entry-level role and a 30% pay cut.

What could have possibly made this seem like a good idea?

Twelve months earlier, the small consulting company I was working for had been acquired by a larger media company. I didn’t have any equity, was having to navigate a much larger org, and was working remotely after a move to Boston.

I loved building with a team. I wanted something in Boston, where I could continue building and get the equity, and potential upside, I had missed out on.

A shift to startups felt like the right next step and I set out looking for the right role at the right company.

I decided that product management made sense. It aligned with my experience leading engineering teams and understanding the needs of the customer. I put a 3-ring binder together with examples of my work from my previous role. (I still have it!)

This was 2008, and the Boston startup scene was smaller back then.

I went to the first Boston Startup Weekend. I joined a bunch of founders who would get together at Andala Cafe in Central Square once a week. Before too long, someone offered to send my resume to a senior partner at a well known venture firm.

Shortly thereafter, I had interviews at 3 companies who had recently raised their series B round.

One company stood out right away. My first interview lasted 2 hours. I connected with the people I met. We dug into the challenges the company was facing, and I was genuinely excited about the problem they were solving. It just clicked.

The only thing was, they weren’t looking for a product manager. They didn’t even have a product team.

What they needed was for someone to join the customer success team and help customers through the onboarding process.

I weighed it against the other offers and decided to go for it. While it wasn’t the role I was looking for, it felt like the right company.

It wasn’t a bad decision.

The company was HubSpot, and I joined just after the B round as employee #30.

HubSpot wasn’t HubSpot yet. It was just another tech company with 200 customers and a fresh infusion of capital. It was a big step “backwards” in my career trajectory.

I took the job as an Inbound Marketing Consultant and moved onto the newly formed product team 6 months later. I spent almost 5 years working and learning at HubSpot. It is the foundation that has made the rest of my career possible.

Every step backwards in a career isn’t going to turn into a HubSpot. However, in my experience, picking the company and team over the role has never gone wrong.

In the past, I have always said, “It was definitely my choice.” Like any other option would indicate failure.

But was it really?

A colleague recently asked me what prompted me to take time off, and if it was my choice.

Which got me thinking.

One of my breaks was taken after 4 years at Owl Labs. I was exhausted, and on the verge of burnout.

I started the job 8 weeks pregnant. We launched the product 6 months later, and then a few weeks after that, I gave birth. I often say that I launched two products that summer. I went straight back to work, taking almost no time off, which was terrible for my mental and physical health. (Why I did that is a story for another time.)

When I chose to leave Owl, there was no option but to rest. I gave myself 3 months of time off from anything work related. I worked out, I read books, and I took a statistics class. It was summer, and my kids went to camp and spent the afternoon with our nanny. I didn’t feel guilty at all. I needed the rest.

It was my choice, and it was also the only choice.

My other break was during a job search that wasn’t going well. I had been looking for a few months, and was getting job offers, just not for the roles I wanted.

It was clear to me that I wasn’t showing up the way I wanted to. I was the problem, not the job market. I needed to take a step back and rethink what I was doing.

I took 9 months. I dove headfirst into women’s health, something I was passionate about, and put job hunting entirely on hold. My ability to do this was a privilege, and I am grateful for the option.

It gave me the space to figure out what I wanted, and how to ask for it. It was also a choice. And in hindsight, I could argue it wasn’t really a choice.

I used to insist it was ‘definitely my choice’ because I was afraid of the alternative. But I’ve realized that admitting you need a break isn’t a sign of weakness, it’s a sign that you are self-aware enough to take care of yourself before you break.

Whether it was my choice or something I had to do, the result was the same: taking a break when I needed to has made it possible for me to show up as the best version of myself, and the leader I want to be.

At the time, we were struggling with customer churn. It was 2009, the market had crashed, and companies were cutting all non-critical expenses. We realized if customers had their leads in our system, they never left. We needed to give them more reasons to keep their leads in HubSpot and more things to do with them.

There were a lot of tools to build. Marketers want to be able to make lists of their leads and put them into groups based on key characteristics. They also want to be able to email them and set up nurturing campaigns.

I was the product manager leading the efforts, and we argued extensively over the correct order to build the different functionality.

Do you want list creation first? Even if you can’t do anything with the lists you create?

Or do you want email marketing first? Even if you can’t segment your audiences?

We decided to build basic lead nurturing first, where you could nurture all your new leads with a simple drip campaign. We were then going to build list creation, so you could segment the leads into different campaigns. And lastly, we would build email marketing to send one-off emails. Most marketers already had email marketing, so the list creation and lead nurturing felt more differentiated.

We had built the lead nurturing MVP and just kicked off a new sprint to get started on list creation when there was a board meeting. I don’t know exactly what the board said, but I do know they were not pleased with our plan. In the middle of the meeting, Brian Halligan came out of the board room and told me to stop building list creation, to start building email marketing, and to have an MVP launched in a month.

This was the only time in my memory at HubSpot that Brian, or the board, told me what to build. Brian obviously had a lot of input into our roadmap, but he also gave us significant autonomy to make the decisions we felt were right. Clearly, something had happened in that board meeting, and we had no choice but to react.

We jumped right in, and a month later, released our first version of email marketing. It allowed you to send a plain text email to all of your leads, and it had a 70% success rate. Meaning only 70% of the emails you sent got where you wanted them to go.

It was the shittiest of MVPs, and we iterated, adjusted, added new features, and built something people actually wanted to use (and which actually got the emails where they needed to go!)

For years, that 70% success rate felt like a personal failure. It took me a decade to realize that what we were trying to do was become a marketer’s all-in-one tool, and for marketers, email marketing is a must-have. Everything else is a nice-to-have. We didn’t need a perfect email tool; we needed our customers to have confidence that we could be that tool for them in the future, so they would import their leads and stick around.

Shipping that shitty MVP was the first step towards earning the right to build the great version later.

We all have our own pandemic stories. It was a scary time filled with uncertainty, and there were moments of learning and growth.

My family moved from Somerville to the woods of Connecticut, where I grew up, and my parents lived. My mother, who had been an art teacher early in her career, volunteered to teach my daughters (2.5 and 7 at the time) for 6 hours each day. They had a few wonderful months of project-based learning. My older daughter recently told me she remembers the pandemic as a wonderful vacation with her grandparents.

My husband and I set up desks in my father’s studio and, during “school time”, did our best to focus on our work. As life as we knew it changed rapidly, it was not easy.

At Owl, in early 2020, our strongest market segment were tech companies with hybrid work cultures. As they all immediately shifted to remote work, our sales plummeted. In April, we started talking about layoffs, and I was given a sales target for the month. If we could hit the number, I could avoid having to layoff half my team.

Within a few weeks, it became clear we were going to hit the number. But in order to avoid layoffs, I had to figure out why sales were still happening and ensure we could keep the momentum going.

I spent a weekend digging through the data. I was motivated to figure out what was happening and avoid cuts that would hurt the business and team.

The takeaway was pretty clear: our target market had shifted. We were no longer selling to tech companies; we were selling to industries that had not fully embraced remote technology and couldn’t afford to be fully remote. Manufacturing, legal, healthcare, and education were adding Owls as fast as they could, trying to figure out how to send as many people home while keeping things moving.

• Doctors set up Owls on their mobile carts so that parents at home could join rounds remotely for their hospitalized children.

• Lawyers bought Owls into the courtroom, and the first post-pandemic court case was held using a Meeting Owl.

• Private schools got kids back into the classroom by leveraging Owls and having hybrid classes.

At Owl, we pivoted all our marketing within a few weeks. By May, we were on plan; in June, we doubled our plan. We learned quickly, we moved fast, and we avoided layoffs. The business had a breakout year, blowing through all expectations.

The pandemic was a scary time, and we will all be processing the experience for decades to come. I learned valuable lessons about creating a safe, loving space for my children during a global crisis and about navigating a team and business through immense uncertainty.

I’m proud of the revenue we hit, but I’m prouder that we kept the team whole. It was a brutal reminder that when the world changes overnight, the only thing that saves you is the willingness to admit your old plan is dead and the grit to figure out what to do about it.

We would build an MVP over the course of a handful of sprints, get it in front of users, iterate once or twice, and then move onto the next product. We were building fast and furious, laying the groundwork as the single solution for all of a marketer’s needs.

At some point, we were working to reduce customer churn and had determined that the best way to keep customers happy was to build tools that would allow them to manage their leads and take meaningful action to move them to customers.

We needed to make progress quickly, and it was decided to add another scrum team to the efforts. I was asked to product manage the efforts of both teams and build list creation and email marketing at the same time.

I was the only PM asked to lead two teams, and rather than seeing this as a vote of confidence in my abilities, I was a bit pissy about it.

The suite of tools we were building was called the middle of the funnel tools because they helped move people through the funnel from lead to customer.

I started calling middle of the funnel….MOFU.

It stood for, Mother F***ing Middle of the Funnel

Because I was pissy (and honestly a bit immature).

And it stuck.

The marketing team took it and ran with it. They then coined TOFU and BOFU, and people at HubSpot started using the terms.

About 10 years later, I was hired at Owl Labs and tasked with launching the Meeting Owl. I started to brush up my marketing skills and was shocked to realize that MOFU had turned into an industry term.

An industry term that I coined because I was feeling a bit pissy.

Originally posted to Linked In

It was 2014, and I was working at Quantopian. Our platform let people write and test algorithms that invested in the market. We needed to build a research platform so our community could explore ideas and data before they wrote new algorithms.

We had a theory that we should use an open-source project called iPython (now called Jupyter) and create a custom iPython research environment for our community.

This was going to be a significant lift, and we weren’t entirely certain that iPython was the way to go. It was a fairly new project, mostly used by lab researchers, and we weren’t sure our community would like it.

The question was how to test this out with as little engineering investment as possible.

We decided to launch the product, with nothing more than the GIF above and a landing page. We set a goal for the launch, announced it as “coming soon,” and encouraged people to sign up for our alpha as the call to action.

Within a few weeks, we had the answer we needed. People loved the idea of an iPython platform. We had thousands of people signed up for the alpha and got building.

It was the most minimal of MVPs.

Originally posted on Linked In

It’s possible it comes from my parents. My father’s work requires lots of tinkering. There is always a first attempt, which sometimes works and sometimes doesn’t, and always looks a little odd. Then he iterates, sometimes for years, before the sculpture is complete.

It is also possible that my time at HubSpot helped hone the skill. The team I was product manager for was tasked with creating the first version of new products. We would create something, iterate for one or two sprints, and then move on to the next product. I created a lot of shitty MVPs which were then refined and polished and rebuilt later.

It’s a skill I mostly find useful, and I have learned that at times, revision is necessary.

I can move too fast. I get excited about whatever I am creating, not take a minute to review what I have done, and send off something full of typos and mistakes. I’ve learned it’s better to write, sleep on it, read it once, proofread with AI, and then send it off.

I took a job as an investment banking analyst out of college. It was the wrong job for me for a number of reasons, but one piece of feedback I would get was that I lacked attention to detail. I moved too fast, I sent my work too quickly, and any errors were unacceptable in that environment.

My love of putting something down and getting started can also cause me to step on other people’s toes. When I’m working with someone who ponders. Someone who considers what needs to be done before writing anything down, I can roll right over them, get the draft started, and never realize they had something in progress.

Is it a skill? Or a personality trait? I’m not sure, and I am interested in where others find themselves.

Do you enjoy writing the first draft? Or would you rather give feedback? Do you find it helpful when someone starts something, no matter how shitty? Or would you rather they refine a bit before sending it your way?

Originally Posted on Linked In