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Transcript

E07 — Trusting Your Intuition with Jamie Undrell

"All these things, they start with a sense that a role isn't necessarily right for you. <...> that intuitive sense at the start is something that is worth listening to."

Jamie Undrell built his business the old-fashioned way. As a tutor, he built a basic website with exam materials that could be useful to his own students without trying to come up with a grand vision of changing the world or raising venture money.

Over the next few years, SaveMyExams proved to be helpful to far more people than just Jamie’s students, and it became a profitable, growing business it is today, helping countless students prepare for their exams.

From the start, Jamie wanted to have the option to step down from running the company if he chose to do so. Eventually, in 2024, he promoted his COO Constance to the CEO position, moving into a chair role himself. At that point, the company was about 80-strong, but Jamie started to prepare for the potential transition when he had only about 30 people on the team.

In our conversation, we discuss how he approached the CEO succession process as an independent business owner. This is a slightly different process compared to stepping down as CEO of a VC-backed business, negotiating it with the board. However, the key principles stay the same: it’s easier to step down if the business is doing well, it’s easier to trust an insider as a CEO candidate and it’s best not to rush the process.

And, shameless plug, I was coaching Jamie throughout the transition, as he explained in the episode:

working with you as a coach <…> was a really good way to mitigate some of those risks, you know? I think one of the things I try and do is always work with people who've been there and done that and know what great looks like. And you've not only lived that but also work with a bunch of people who've gone through that process.

Enjoy the conversation!

Timestamps

(Clickable on YouTube)

00:00 Introduction

01:46 Founding Story of SaveMyExams

03:35 The Decision to Step Down as CEO

05:57 Starting the Transition Early

09:01 Mitigating Fears and Concerns

10:59 Internal Vs External Candidates

15:15 Adjusting to the New Role as Chair

17:00 Impact on the Team and the Business

19:25 Personal Reflections and Advice for Founders

30:24 Future Plans

32:38 Conclusion and Key Takeaways

Unconditionally Human
Startup CEO Succession
Real stories from founder CEOs who stepped down, professional CEOs who took over from them and VCs who saw the process from the inside.