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by pfitzsimmons 4173 days ago
I went through this exact situation. I joined a company when it was just the founders and me, and then we grew to dozens and then hundreds of people. As we grew, I felt these same slights: I was left out of strategy meetings, I was not mentioned on the website, managers were hired over me, etc. Overall, it felt disconcerting as more and more happened outside of my control, and without my knowledge. At first I was frustrated, then I realized I had the best of all possible situations.

Some notes:

1) If you do not have much experience scaling a team, then it is sensible for the founders to bring in someone with more experience. Scaling team requires more than just hitting deadlines. It is about recruiting, retention, recruiting, managing personalities, career growth, recruiting, managing up, communicating across teams, etc.

2) Everyone's role changes as you grow, for better and worse. For instance, early on the VP gets to have fun setting direction and designing the overall product and strategy. Later on the VP might be spending 90% of their time dealing with conflicts, recruiting, firing, managing up, etc. They may long for the day when they got to play a big role in product development. Early on as engineer, I had the benefit of being able to build an entire product by myself. Later on, the advantage was that I could take vacations and did not have to deal with bugs and outages 24/7.

3) You will have to specialize to some extent. You cannot be the jack-of-all trades role forever, no one can. If you want to eventually have a VP/CTO role, then you will need work with your VP to develop your management abilities. For instance: ask for mentoring, start reading books and articles on management, ask to have a junior engineer put in you, help out with interviews and recruiting. (Note to actually get a VP role, you will probably have to switch to a smaller startup in a few years, using your cred from this gig to get you the job.) If you want to do greenfield development, work with your VP or founder to carve out a role building out innovative/experimental/skunkworks features. If you want to do scaling and architecture do that. There are lots of ways to interesting work and build valuable skills, but you are going to have to choose a course. (In my situation, I alternated between doing experimental/greenfield features and doing scaling/rewrite work on existing tools.)

4) With regards to customer facing roles, I highly advise that your company have a policy that every engineer spend a half-day in support at least once a month. It is essential that developers stay connected to the customer, both so that you can intuitively understand how to solve their problems, and to increase your empathy and motivation.

5) Try to figure out a way to get looped-in informally to the strategic aspects of the business. Make some sort of effort to have lunch or beers with a founder once a quarter. If you have 1:1's or have a wiki where decisions are discussed, then that can be a good thing. The execs understandably want to keep management and strategy meetings to a small number of people, otherwise the meetings suck. But finding a way for you to informally connect and give your two cents can be valuable both for you and the execs.

6) If you want to raise your profile and get your name known, use whatever leverage you have to get some favors. Ask to have yourself put on the web site as "Founding Engineer." Figure out a way to have the founders to introduce you to useful people, and to help you get into some of the more prestigious invite only events, whatever they are in your area. You have to use judgement and be diplomatic, because you might also lose out on advancement if you are seen as angling for a quick exit.

7) Generally, I would recommend sticking with the company as long as it is on an upward trajectory (unless you have a compelling alternative). You will learn a lot as you go, and your reputation will increase with growth.

Eventually I realized that I had the best of all worlds. Why does one want to be a VP? Usually money and status. What sucks most about being a line-level employee? Lack of agency/control. But in many ways it is less fun to be a VP, than to be a high-status engineer, who has enough sway to avoid micromanagement, enough credibility to control his or her own destiny, who can spend their time working the craft that they love. As engineer #2, you get status by virtue of your early employee number, and hopefully and you will get good money from equity stake (if not, then that is truly unfortunate). So hopefully you get the money/status benefits of being an executive, while still getting to work your craft, and still getting to stay in a peer relationship with your fellow engineers.