Startup CEOs Need to Be Involved in Sales and Accounts Consistently to Refine Pattern-Matching

In my experience there are two types of entrepreneurs.

One type is solving a problem they have for themselves, and hope that others have the same problem. Sometimes this work out very well -- Linux Torvalds creating Linux is a big obvious example of this.

Other types are constantly pattern matching. As part of creating their vision, they have often had dozens, even hundreds, of conversations in order to create their vision. They understand deeply the pain of their market, and are constantly looking to build a pitch and refine it based on that pattern matching.

As you start to gain traction in your startup, however, things start changing:

- market conditions shift, causing your customers to act differently

- competitors enter and leave, with different focuses

- your target market itself may not be "healthy", and you hadn't considered that.

The problem is not the change itself, but more that the CEO is no longer deeply involved in pattern matching as the company grows -- there's no time. You are busy fundraising, hiring, training employees, closing deals, putting out fires, writing presentations, answering e-mails. You get busy being productive.

All the while, your market is changing. And you're not seeing it. It's not that your employees aren't good. It's that you trained them to look for the market problems 3-4 years ago and not for tomorrow's market problems.

As a result, instead of tweaking your Vision, Mission, Strategy, Market Problems, ICP incrementally over time, the opposite happens. Your ICP becomes stale and unfocused. Your market problems stop resonating.

New problems start appearing, but they look like distractions and not opportunities. Even if you hear them from your staff, unless you as a CEO experience them first-hand, sometimes you are not motivated to keep improving your goto-market based on this new information. Because you haven't pattern-matched it yourself.

I see this all the time, and I have been victim to it. For earlier stage startups (let's say pre-Series B), one question I always ask CEOs is this:

"When is the last time you were on a sales call?

Who are your top customers?

How often do you talk to your top customers?"

Sometimes I get silence. Sometimes I get old-time customers they have the best relationship with. Rarely do I hear high ACV customers that just signed up in the last 6 months.

Sometimes I hear a list of top customers that doesn't match their ICP, or matches an ICP from 5 years ago.

At an early stage startup, your team is more junior. They are not always thinking independently, and they are most certainly not entrepreneurs.

When the CEO listens to the same conversations, they can easily say: "Woah. Something's different here, this feels wrong. Maybe we should rethink our approach." Remember -- No one else in your company can say that. Stay involved in your market.