The hardest part of working at a growth startup is having to re-interview for your job every year. The challenge of scaling You’re heading a key function at your 25-person startup. Maybe you’re head of engineering; maybe you run marketing. Hell, maybe you’re the CEO. You kick ass and your startup grows fast – and with that growth, the needs of the company evolve. Things in the new world are now going okay, but perhaps not optimally. Eventually, the CEO and board of directors get in a room to discuss what to do.