How To Use Jackson’s Matrix To Make Startup Hires

Tim Jackson
Lessons From CEOs
Published in
9 min readSep 20, 2019

An executive’s idea of a wise investment in your startup’s growth?

A simple two-by-two approach to decide what kind of people to recruit for a growing startup, and to avoid the most expensive hiring mistakes

When founding my first serious startup, I made enough mistakes to fill the Encyclopaedia Britannica. But the most useful early mistake, as a learning opportunity, was that three of my first four hires were gone within ninety days. One of those was the head of marketing — let’s call her Michaela.

Michaela had a stellar CV. She’d been to a top university. She had a decade of career experience in the industry. And she’d worked for two of the top agencies in the world. She was way out of our league, and so expensive that the only way we could bring her was to pay half her current salary and to give her a huge slug of stock options to outweigh the loss of the other half.

Yet a couple of months after Michaela joined, things weren’t going well. We had no more customers than before, and while lots of strategies had been developed, we didn’t seem to actually be doing any more marketing than before. The dissatisfaction was mutual: by then, Michaela had had second thoughts about the half-equity deal she’d done. Within a few weeks, she was out of the door. (It was a decision she probably regretted, since the equity she left behind was later worth $10m.)

But Michaela wasn’t the biggest hiring mistake we made. When it came time to take the company public, I felt we needed a CEO who knew how to talk to Wall Street. So we recruited an authoritative, impressive guy who when you met him gave you a strong feeling that the boss had just walked in the room (even if the boss was in fact still you).

He declared his ambition was to ‘professionalise’ the business. In this, he fulfilled all our hopes. Wall Street was impressed. We were able to IPO the business on the NASDAQ. And within a year, we’d acquired our biggest competitor for $1bn.

There had been changes inside, too. The senior people started flying business class rather than economy. The company moved from a cheap and grungy warehouse to a glass and metal tower. And the new boss’s BMW sports car, paid for by us shareholders, had its own reserved parking space in front of the entrance, so people practically had to walk around it to get into…

Tim Jackson
Lessons From CEOs

Startup founder, former Economist and FT journalist, CEO coach, and seed VC at