Many of you have worked at, supported, or know someone who has worked at an early stage startup. Or maybe you're a VC backing companies at that stage. Startups with 20 people or less. You know what I'm talking about.
If you were ever a part of that world, you've probably experienced firsthand how energized everyone is around the vision, mission, and product. How easy it is to get things done. To work with others. To communicate. How much autonomy you had around the tools you used and the initiatives you pursued. The camaraderie. The feeling that you're all one team. The shared struggle of working toward product-market fit. The collaboration around experimentation, and how that naturally translated into next steps, regardless of function.
What gets done feels intuitive, and the entire company seems to run on shared awareness.
Goals feel shared. Everyone understands what matters most and how their work connects to it. Progress, or lack thereof, is visible. If something isn't working, it's usually possible to pinpoint why. Failure at this stage is most often tied directly to product or strategy.
Now if you've stayed with a company as it grew to around 100 people, or joined one at that size, then you've probably felt the shift. There's a stark difference between how things work in a 20-person startup and a high-growth organization.
As companies grow, distance grows with them - between teams, decisions, and the work itself. More people means more specialization. More layers between the vision and the day to day. More coordination is required to get even simple things done. New leaders arrive, formal and informal processes begin to take shape, and functions develop their own rhythms. The vision may still be there, but it's less clear how it turns to strategy, and how strategy turns into aligned actions across the organization.
Frustration starts to show up. Things not getting done gets blamed on other teams. Turf lines emerge where shared struggle once lived.
And one thing becomes painfully clear: the default systems being built multiply faster than clarity does.
Clarity around what's actually driving results.
Clarity around how decisions are made.
Clarity around who owns what.
Clarity around why targets keep getting missed.
Clarity around how goals connect across teams.
At 20 people, progress was visible and intuitive. At 100, progress requires coordination and design. Without that intentional step back to coordinate how work gets done, the excitement that once fueled the company turns into friction. Shared missions turn into turf wars. Instinct turns into process. Closeness turns into distance.
Failure at this stage is rarely product or strategy. It's usually about how the organization works together to build and deliver it.
Because at 100 people, companies need shared systems, not just shared awareness.
And what feels like dysfunction is often just the moment where instinct stops being enough.