80 hours, 5 offers, and 1 new job: how I pivoted into fitness tech

In summer 2021, I left Google for a role in fitness tech. The job search process was exciting and scary, and consumed over eighty hours. In the end, I had five offers, a handful of rejections, and a difficult choice to make! In this article, I walk through how I approached the process of a field-specific PM job search, including tactics for getting in touch with companies and evaluating offers from companies of different sizes. Because I had to lean heavily on mentors (thank you 🙏 !) to figure out my approach, my hope is that this info makes the process a bit more accessible.

#1: Identifying and testing my main career hypothesis

After reflecting on when I’ve felt most happy and energetic, I realized that I’m a pretty mission-driven person. My longest-standing interest has been in fitness, though there are other areas I care about, like mental health and social impact tech. So, I developed a career hypothesis that I would feel motivated and fulfilled working in the fitness tech space. I started soft-testing that hypothesis by spending my weekends writing this blog and by being a “20%” PM on Google’s internal fitness startup in early 2020. I felt fulfilled and energized – strong proof for my career hypothesis.

You’ll notice that this career hypothesis isn’t an inclusive prioritization framework: it doesn’t say anything about compensation, company size, or having my own startup. This is intentional. In omitting these things, I was explicitly stating that being in fitness tech was the first order cut I would make. All other prioritizations would follow.

#2: Identifying 25 companies that aligned with my hypothesis

Now that I knew what I wanted first, I wanted to identify the companies in the space I was interested in. In addition to the ones I knew about already as a user and through conversations I’d been having just through my interest in the space, there are some specific tactics I leveraged:

• I searched on LinkedIn and Google’s job search for product management roles with keywords like “fitness,” “nutrition,” “health,” “strength,” “cardio,” and “sleep.”
• I Google-searched for “fitness tech companies” (and related keywords) and browsed the “Top” lists that showed up, like this Built In list and this AngelList list.
• I found companies in the news at various fitness tech mailing lists, like Connect the Watts and Fit Tech. 
• I also looked at all companies that had or were projected to IPO in 2020 and 2021 (via articles like this). I wanted to make sure I didn’t miss any high-growth companies that fit my criteria, or non-fitness tech with compelling missions.

I ended up with twenty-five companies – from seed startups to public companies. Filtering on location and presence of open positions left me with eleven companies at the end. Two caveats:

• While I also only looked at companies with PM openings, I wouldn’t recommend filtering on this — reaching out to people at the company to see if roles are coming up or could be created for you is a valid strategy. 
• I didn’t filter strongly on company size, but it could make a lot of sense to do so, as size can dictate the type of role, speed-of-operation, and culture.

#3: Getting in touch with 11 companies

I had informal discussions or first round interviews with hiring managers at all eleven different companies. Here’s how I was able to get my foot in the door, in order of what I found effective:

• Leveraging my existing network: In some cases, I already knew folks at these target companies because of my interest in the space. I also asked friends and close colleagues if they knew anyone at the companies. Sometimes, supportive people who knew I was looking proactively offered to introduce me to people at their companies. One key tip here is to be forming this network ahead of time, even when you’re not looking for a role. It’s interesting to learn from new people, helpful for when you’re looking for your next thing, and increases your overall awareness of the current market’s opportunities.
• LinkedIn cold reach outs: I sent LinkedIn connection requests with notes, and occasionally InMail, to hiring managers and PMs at these companies. I cited my background and passion for the space, and sometimes observations about the specific company’s products — and people were surprisingly open to chatting with me.
• Cold resume drops: I applied to several job postings with a blind resume drop. This worked out for me in one case, though it’s often a long shot. Roles can have hundreds of applicants, with referred or flagged-through-network resumes at the top of the pile.
• VC talent pipelines: I didn’t really lean on this strategy, but I’ve heard that folks have success by reaching out to the talent teams at VCs, who may then introduce you to portfolio companies who are a good fit.

A big acknowledgement here is that I was privileged to have had the Google network and name brand recognition behind me. For example, this helped when reaching out to people who were ex-Googlers themselves. Not everyone starts from this place, but I do think that anyone can take steps toward building communities and reputation in the field they’re interested in. For me, my passion in this field had led me to become a certified personal trainer almost 6 years ago, and my writings on this blog showed I could think deeply about the space. I made sure to use these related accomplishments to frame my value.

#4: Onsite interviews with 5 companies

Of the eleven companies I talked to, three rejected me after the first round, and I chose not to proceed with three others. I went to onsite interviews with the remaining five. All five had some kind of written assignment, whether that was answering a prompt like “You are the PM for X; what do you do?” or “Tell us in detail about a project that you are proud of.” The written assignments were generally presented live to a panel, and followed by other interviews with situational and behavioral questions.

I took a lot of care to share my values as a PM:

• Empathy: caring about the user’s problems, and about each other as a team.
• Hypothesis-driven: strong, (dis)provable beliefs driving product decisions
• Transparency in teamwork: bringing each other along from the start, such as on decisions, and being honest about the situation and plans.

Making my PM style clear would select for places that would value my approach.

#5: Choosing an offer to sign! 

In the end, I received offers from all five of the companies I onsited with. It was going to be a difficult decision — my options ranged from Series C startups to public companies, and from connected hardware to wearables to app-only. To frame my decision, I built out a one-slide framework. Here’s a template based on that framework (with all info removed – the colors are random!) that you can feel free to copy for your own use. You’ll probably need to modify it to capture your own criteria!

I gathered information to fill in the framework through meeting with the teams at each of these companies, reading on Glassdoor, trying or watching demos of the products, and reading public news about these companies. Here’s how I thought about each of the columns in my decision, and some example questions I asked:

Interest in the role’s topic: I wanted to be excited every day by the subject matter of the role. I asked myself:

• What are the biggest problems I’d solve in this role?
• How do I feel when I do a visualization exercise of me in the role?

What I’d learn: I knew I wanted to operate with tons of responsibility in a faster-paced environment. I wanted to be working on a growing program with direct revenue impact, and to learn more about pricing and growth. I asked hiring managers and team:

• What does success look like in this role?
• What are the biggest things you’ve learned so far on this team?
• What are some of the things you don’t know yet?
• Why are you hiring for this role?

Company’s business positioning: joining any company is a calculated risk. I wanted to make sure I understood the strategic moats and risks for each of the companies. 

• I asked myself: Could big tech (Apple, Amazon, Google, etc.) enter this space and immediately gain an advantage through their lower margins and existing distribution? What strategic moats does this company have, or is trying to build out?
• I asked team members: What are the biggest risks facing your company?

Rapport with manager, team, and culture: people matter a lot, and I wanted to make sure I’d be set up for success in terms of environment.

• I asked hiring managers: What’s your management style? What’s an example of a time you helped a report reach their career goals? What are your personal career goals?
• I asked team members: What’re the biggest reasons not to join the company? How do you usually work with product managers? Via LinkedIn, I also asked employees who had left the company about their experiences.

Compensation: comparing offer values, especially across startups and public companies, was hard. While compensation varies at different sized companies, one useful industry benchmarking resource is levels.fyi. A helpful article and startup equity calculator is Carta’s here. Here’s how I approached getting to a “Total Annual Comp” value:

• Base salary: this is your guaranteed money! It’s valuable to understand how and when raises are calculated. I conservatively modeled a 4%/year raise.
• Target bonus: does the company have a target bonus for performance? Lots of startups don’t.
• Signing bonus: will a signing bonus be offered? Can you negotiate one?
• Equity value: to calculate the value of equity (in the form of Incentive Stock Options, or ISOs), I used this approach:
  • Calculate the current value of the options. The strike price (aka exercise price) is the price you buy the options at. The preferred price is the price investors paid in the latest round of funding, and can be thought of as the aspirational value those shares can eventually be sold for. With ISOs, you have to pay the strike price to get shares that could be sold at the preferred price – though of course there is no guarantee how an IPO will go. So the first thing to calculate is the strike-price-adjusted stock option value: (the number of options awarded) x (preferred price – strike price). This article has more detail.
  • Model dilution over future rounds of funding, assuming 20% modeling over each round away from an IPO. For example with a Series C company, I expect at least a Series D and E raise before IPO — and some companies have additional rounds or even bridge rounds. So I calculated the dilution-and-strike-price-adjusted stock option value: strike-price-adjusted stock option value x (0.8 ^ # of series to be raised). (It’s true that the total valuation could go up with new rounds, but I didn’t model that in this step. Read more about dilution here.)
  • To get to the annual comp, I divided the dilution-and-strike-pride-adjusted stock option value by the vesting period, typically 4 years. I also sometimes modeled future growth: for example, if the preferred price were to triple. You can do this by repeating the above calculation but multiplying the preferred price by the projected growth factor.

Another factor to consider is equity percentage. You can read more about what equity percentages to expect at different company stages here, and benchmark against real-world data at AngelList. One last thing to note about equity in startups: this is a high risk/reward component of your salary, because it might not IPO, or not for many years, or not at the price you expected.

#6: Following up with hiring teams

I ended up talking with over 50 people during the interview process! It was really important for me to follow up with everyone, from panel interviewers to friends who introduced me to friends. They had invested time and belief in me! It was only right to let them know firsthand of my eventual decision. And I meant it when I told folks at the companies I declined that I hoped we’d be able to work together someday.

One mistake I made was not updating the various hiring managers during the offer decision period. As I gathered new information, I’d been continually refining my view on which offer I’d take. But I didn’t keep the hiring managers posted, leaving them thinking based on our last conversations that I was thinking favorably towards their offers. When my decline calls were surprises to them, it became clear to me that I didn’t set the right expectations.

End to end, the whole process took about one month. I’m really happy with ending up at Peloton — not only because I’m loving my first few weeks on the job, but also because I know I approached my search rigorously, exhaustively, and proactively. In the end, it’s most important to me to have peace of mind that I made a thoughtful decision.

Here are some related topics I didn’t cover in this article but could in the future — drop a comment below if there’s one you’d be particularly interested in hearing about!

• Why I decided to leave Google, and how I knew it was time to leave
• How I timed the offers to (roughly) line up with each other
• Why I didn’t want to start my own thing (at this time)
• How I decided not to proceed with certain companies
• Why I think I was turned down for some roles, and if/how I would have approached those conversations differently
• The different “types” of PM roles and how to determine which type you want (or that a role is)