First PM at promising startup: Accelerator towards fame, wealth, and glory or not worth it?
The 1st PM is an interesting role. While there's a ton of autonomy and flexibility, there is also ambiguity, frustration, and potentially unrealistic expectations. So, is it worth it?
(Teddy the Corgi, San Francisco, California)
Note: this is a re-post from an original LinkedIn post I made years ago while I was at Thumbtack growing from 1st PM to Head of Product for Pro.
The role of the first Product Manager of a company is a tricky opportunity. You’re not the founder. You may not be the head of product. Combine the “wear all hats” philosophy of product management with the super resource constrained environment of a startup, and you’re really the de-facto wear-all-hats-task-monkey. Is it worth it?
What are you getting into?
The first PM role does not start out as glorious role. It has a lot of random parts, from writing SQL, to taking support calls, ordering team lunches, etc. It only has weight after your company has “made it” in the eyes of others. Similar to being “one of the first 20 employees”, being the first PM often only matters if your company is now more than thousands of people with more than $100 million in revenue. Before that? You’re just a minnow.
The role for a first product manager is often created after a company raises a seed stage or series A. At this point the founder or the head of product has gotten the company to a place where early adopters are using it, and hopefully some revenue is coming in the door. It’s now time to get into the upward swing of that dreamed hockey-stick growth.
That’s where the first PM comes in -- to give the founding team bandwidth to focus on other vital tasks like doubling in headcount and longer term strategy (six month rather than six week). In Thumbtack’s case, there was a 20 person engineering and design team, and the VP of product and co-founders were working 80+ hours a week. So they decided to hire someone to help with a portion of the product and address a specific user problem -- a role that seemed clearly defined at that moment with plenty to do.
When in one’s career is it right?
For the most part, unless the founding team has “street cred” (e.g. repeat founders, senior leadership from famous companies), the first PM role tends to make sense only for early career candidates. Why?
You’re not the head of product or founder, which means you are the executor. This appeals much less to more senior PMs.
The scope of the first PM often starts out small as it’s a portion of an early stage, smaller scoped product.
You’re not working with or learning from industry veterans (yet).
All-in cash compensation tends to be lower than entry level at bigger companies (in return for potential giant equity upside...more on this later).
In my case, I had very little product experience outside working with a contract dev shop for my own wine e-commerce startup. Thumbtack took a leap of faith and brought me in without much product experience, and trusted me to learn on the job. While I could’ve taken more senior roles that are more directly related to my past experience at the time (e.g. business operations, strategy, or consulting), it made sense for me to take the leap to break into product and see if the role was a fit.
Take a seat on a rocketship. And ask for seat upgrades.
As the first PM, you are first in line to take advantage of the opportunity when the proverbial rocket ship takes off. But then there’s actually taking the opportunity. I’ve seen many people miss this: they assume that as the company grows, opportunities will just drop in their laps and they’ll be given the bigger role. That rarely happens. In fact, as the overall engineering and design team grows, your team may just stay the same size. You actually stop growing in scope and instead the company hires more product managers to cover those other areas and then eventually asks you to hire your own manager. The truth is, career growth will not happen unless you proactively develop new interpersonal skills and ask for growth opportunities.
As a result of company growth, the skillset the company asks for from its product managers evolves. Interpersonal skills become much more important: building relationships with all those new hires across different functions, learning what these new functions are, actively managing communications and seeing ahead of the curve on product roadmap conflicts. Strategy setting and getting buy-in is no longer simple process involving 2-3 other decision makers. There are many other functions or product teams to coordinate with. In fact, other product teams now have their own goals and metrics that may conflict with yours.
Meanwhile, for the first PM, it's easy to remain narrowly focused on execution because, well, historically the company would have gone under if features didn’t ship. The natural flow is to design, ship, measure impact, repeat. As a result, you neglect to develop the other skills that become important to the PM role at bigger growing companies. Particularly for early career product managers who may not have managers watching out for them on this front, it's easy to fall into this trap.
All of a sudden, as the org explodes in size and complexity, you find yourself increasingly alienated in terms of influence to your small part of the world. Your leadership sees that and interprets it as a lack of ability to drive large roadmaps. At the same time, the company can now afford to hire more experienced PMs who offer the “I’ve seen this before” or "I've worked with big teams" coin. In fact, the more successful in a short time period a company is, the more likely this occurs. I was lucky to have mentors at Thumbtack and externally who pointed these shifts out to me, so I was able to evolve with the team.
In addition to expanding your skill set, it’s also critical to actively look for opportunities to show you can do that will help up level your role. Show you’re interested in growth -- ask (and show) how you can help and start having those career development conversations most startups with a handful of people don’t have. For me at Thumbtack, it was as simple as bringing it up as something I was interested in trying to do during a one-on-one with my manager. Don’t only volunteer to lead things you already know you can do well. Take a risk and try for things you’ve never done before but are important for the company. For me, I’d never done a brand launch or built an Android app before -- but the opportunity came up, and I asked for it.
Build your brand - wear one hat smartly
As a company grows and develops structure, it typically starts to look more for specialists than generalists, partly because it can now afford to hire more for specialized skill sets like data science, performance marketing, diversity and inclusion, etc. First PMs tend to have a “I’ll do anything that needs to be done” mentality -- you tend to just pitch in everywhere.
However, when you’re seen as the person who’s good at everything, then really you’re not a leader in anything. At some point, being really smart and just figuring it out stops working -- someone else has done this somewhere else longer than you. Counterintuitively, you actually need to narrow your focus and start being known for something to center yourself within a part of the product or your strengths as a PM.
For me, this meant drastically reducing the non-PM work I was doing (e.g. building more Looker integrations, coding small growth conversion tests, leading hiring for user researchers), and focusing the scope of my PM work to supply side (pro) experience, improving retention of new pros joining the platform, and delivering wins.
At first glance, this may feel a little counter to the two previous points, but it’s not: it’s about finding a balance between focusing on a strength or area, and then building on that strength by grabbing the right opportunities. Don’t just take any opportunity that comes along and try to prove yourself. Be smart about which ones and how they help build your skillset as a leader within the growing organization.
Your Success == Company Success
Perhaps obviously, company success begets career growth opportunities. As a first PM, your career, more than that of an engineer or designer, is a function of success of the company and your own ability to grow with the company’s needs. Your skillset isn’t showcased by a design portfolio or passing coding interviews. You're measured by the impact you’ve had on the trajectory of the company.
When hired, it may have sounded like the company knew exactly what problem you needed to solve, with all the right intentions, but you’ll quickly find that said problem spawned five more problems that are now also on your plate. In fact, solving a few of those problems are now critical to the continued growth and success of the company. And you’re the one directly formulating the strategy and executing it (or sometimes executing then formulating -- aka testing your hypotheses).
Therefore, a successful startup could accelerate your career - it propels you into strategy and decision-making roles that would normally take longer to come by, and future companies are more likely to trust your product instincts at a higher level. On the flip side, an unsuccessful one keeps you in a similar role and, at best, adds to your years as a PM, often discounted against the same years at a brand name place like Google or Facebook where you get some “standard high quality training” on PM basics. In fact, multiple failures in a row will raise questions around your abilities (and sanity).
In short, the first product manager has a direct impact on the growth of the company, which in turn creates valuable opportunities for career growth. It’s then up you to recognize an opportunity and take it, or else the company often looks elsewhere to fill the gap.