From Builder to CEO

I’m going to shift my focus from sales to leadership for the next series of blog posts.

There is a moment in every early-stage company when the founder’s greatest strength becomes the company’s biggest constraint.

In the beginning, working in the business is exactly what’s required. You are either building the product yourself or working closely with a developer and/or a team. You are the one who sells to the first customers. You answer support tickets. You rewrite the pitch deck. You do whatever is necessary.

I can identify with this because I remember in the very early days of my first company, we spun through several people we hired to do customer service. It was such a failure that I took over customer service myself for the next several months. I answered tickets until midnight every night. It was brutal.

However, at some point — maybe around 8 to 15 employees — the equation changes. The company’s performance becomes less dependent on your individual output and more dependent on whether you have internal systems in place and capable people doing these jobs. And that’s where many founders struggle.

It’s true that working in the business feels productive. You are making progress — closing a deal. Redesigning the homepage. You can point to something concrete and say, “I did that.”

Running the business feels different. You’re allocating capital. You’re deciding who to hire — and what their jobs are. You’re setting priorities that will shape the next six months of work. You’re evaluating risk and protecting your cash runway. Oftentimes, you’re deciding what not to build.

At this point, some founders retreat to what feels comfortable — the product, or sales, or some other area that is their forte. And this is where companies stall.

The uncomfortable truth is that if you are still the best engineer, the best salesperson, or the final decision-maker on every tactical issue, you are not scaling a business. And you probably don’t have the right people on your team.

I always look to hire people who are better at a particular task than I could ever be. That takes humility. But it gives you leverage. That’s because the CEO’s job is no longer to produce output. It is to design systems that produce output.

This kind of leadership also creates delayed consequences which may also be a bit uncomforatable and less rewarding. A hiring mistake might take six months to reveal itself. A strategic bet may take a year to validate. A capital allocation decision might matter if sales fall off unexpectedly when markets tighten.

However, the bottom line is this: your value add is judgment. You are being paid for the quality of your decisions. And should you fail to make that psychological shift, the company eventually hits a ceiling — and that ceiling is you.

The founder who successfully makes this transition understands something subtle but critical: the most important work is often invisible. It lies in assembling systems and people that produce results far greater than you could on your own.

If you find yourself exhausted, ask yourself this: Are you still involved in every detail?If so, the issue may not be workload.

It may be that you are still operating as the founder of a startup — in a company that now needs a CEO.