One of the biggest founder dilemmas is about making course corrections while still in the flight. Among them, spotting an early hire who can be groomed for the next life stage of a startup is a difficult task. Add to that the blunt honesty required to acknowledge that someone you hired for the moon mission needs to be de-planed midway because they lack what it takes to shift the startup orbits.
The first few people you get in, you want them to be more of a generalist—people who are builders, who can roll up their sleeves and figure it out. It’s very chaotic, and they are very flexible. We have changed the organizational structure five times. We have built teams that have failed. You don’t want the traditional sales guys who will raise their hands and complain about things not working. Now, we have reached a size where we can hire more traditional sales guys
NOT EVERYONE FROM THE CORE TEAM MANAGES TO SCALE AS THE COMPANY SCALES. THE ENTIRE CORE TEAM (AND NOT JUST THE ENTREPRENEUR) HAS TO GROW FASTER THAN THE ORGANIZATION TO REMAIN RELEVANT. IF YOU WANT YOUR FIRST ENGINEER TO BECOME DIRECTOR OF ENGINEERING, VP ENGINEERING, AND THEN CTO, THEY MUST EVOLVE AT THAT PACE. OTHERWISE, THE ORGANIZATION WILL NOT GROW. HOW YOU MANAGE THESE TRANSITIONS WITHOUT CREATING UNNECESSARY ANIMOSITY BECOMES REALLY IMPORTANT.
since there is more predictability, but the first few had to be unconventional and flexible. In fact, the best thing I ever did—everyone was shocked when I proposed this internally—I moved my director of product to run sales. He is now director of sales! In the product, he had only two people reporting to him. Now he has an organization of 140 people reporting to him, and he hits and beats his number like no other. His first feedback to me was, “Ritesh, probably one of the best things that have happened to me was to move to sales.” It’s also because of him that I have been able to build a scale-up sales team. If I had hired traditional sales guys, they would have never experimented, never taken risks.
Not everyone from the core team manages to scale as the company scales. The entire core team (and not just the entrepreneur) has to grow faster than the organization to remain relevant. If you want your first engineer to become director of engineering, VP engineering, and then CTO, they must evolve at that pace. Otherwise, the organization will not grow. How you manage these transitions without creating unnecessary animosity becomes really important. It is deeply ingrained in the journey of a scalable organization because it creates dynamics that people cannot handle otherwise. Sometimes you will be better off paying this person $1,000 and keeping him as an advisor or in some such capacity in the organization; there are many such techniques through which you can handle scaling.