Learning from a hyper growth startup

Learning from a hyper growth startup
May 18, 2021

I was the first engineer and 3rd employee at a company that grew from a problem statement to a team of over 550 people with a 1.3b valuation in 3 years. I moved from being the only engineer to managing managers of engineers. The company direction shifted, my manager and peers shifted (many times!). The changing definition of ‘good’ gives me that dizzy feeling like after you stop spinning and wobble around - everything is moving and it is hard to tell which ways is up.

This is my attempt at writing out a few things I think are ‘up’.

Managing people in the real world

From the outside, I read books and blog posts on management. I imagined 'people management' as a deliberate set of actions to grow employees and multiply the effectiveness of the team. However, this has not been my experience. At a high growth company like Cityblock Health (in year 2, the team grew 700%), management is mostly reactive. In any given quarter, the estimates for headcount, budget or business needs may be off by multiples.

In startups, your plans are castles in the sand. The business may change in the next few weeks or your role may need to dramatically change. The timelines are severely compressed so you can’t make forward progress while stopping to consult a variety of materials and then design and enact a forward looking strategy.

To cope with this reality, I recommend a few key things:

  • Build a network of peers you can call for advice (and who you support in turn).
    • There is no replacement for a good peer network. I deeply wish I had done that more. Today, I use Merit. In the past I used Orbital Studios and had a management coach.
  • Find some simple principals to will ground you.
    • The ones that still will likely be ones where you made a mistake.
    • You will get pushed around A LOT. That is normal. Practice pushing back by listening and asking questions.
  • Read some management books but know that the job is 80% is just a mess.


I've broken a few lessons into three general categories based on the three directions you need to face as a manager: up, inward and toward your team:

Managing Up
Managing Yourself
Managing the Team

Small things to remember

  • The two things that matter are people and performance. In that order.
  • Positive reinforcement is the most powerful force you can exert as a leader.
  • Always work to make yourself irrelevant.
  • You always can solve other people’s problems if they are also your problem - no matter what lack of autonomy you feel. Make sure your team knows this.
  • Be a force of unbending consistency.
  • Relationships are far more important than you imagine.
  • You can only fully control yourself.
  • Remember the 5 factors of effective collaboration from @Camille Fournier
    • Are you talking to one another effectively?
    • Do you know where you are going?
    • Do you know how you are getting there?
    • Do you know how to tell of you are getting there?
    • Have you done the work to make sure your team can actually get work done?

Short books with actionable information and/or frameworks