When I started Webinse in 2009, it was me, a laptop, and a handful of freelancers on Upwork. By 2014 we had 70 people across engineering, project management, and client delivery.
I learned more about building companies in that period than in anything that came after. I also made most of my biggest mistakes there.
The hiring mistake I made early
I hired for skills before I hired for operating style. I needed engineers fast, and I evaluated candidates almost entirely on technical output — can they build this, do they know that framework, how fast can they get up to speed.
What I didn’t account for was how people operate under ambiguity. A startup at 15 people doesn’t have clear processes, clean handoffs, or documented everything. People who need structure to perform will underperform at that stage, no matter how skilled they are.
The fix, which I applied too late: add a simple operating-style screen to every interview. Not “do you prefer structure?” — everyone says no. Actual scenarios: walk me through a time you had to figure something out with incomplete information.
The systems I should have built earlier
At around 30 people, things started to slow down. Not because people were less capable — because coordination overhead was eating the gains from having more people. Everyone was looped into decisions they didn’t need to be in. Accountability was fuzzy. Projects would get “done” and then need to be redone.
I waited too long to build the operating layer: defined roles, delivery checklists, a real QA process, a way to onboard clients that didn’t require me in every kickoff.
If I were doing it again, I’d start building those systems at 10 people, not 30.
What I got right
The one thing that actually worked well: I built Webinse Academy when I couldn’t hire the engineers I needed from the market. Instead of competing for senior talent I couldn’t afford, I trained juniors myself.
That solved two problems at once — we got engineers calibrated exactly to our stack and processes, and we created loyalty that market hires rarely have. Several of those people became team leads.
The pattern I’ve carried forward: when the market doesn’t give you what you need, build it yourself.
What I’d tell a founder at 10 people
Hire slower than you think you should. Each person you add changes the culture and the coordination cost. Get the operating layer documented before you need it. And train your own people when the market fails you — it’s slower upfront and faster long-term.
The 70-person version of Webinse was harder to run than the 10-person version. That’s unavoidable. But it didn’t have to be as hard as it was.