In this episode, I sit down with Harry Siggins, a former Chief of Staff turned workshop facilitator helping growth-stage companies. After five years acting as the strategic Swiss Army knife for startup CEOs, Harry stepped off the always-on hamster wheel and into a portfolio career focused on what gives him the most energy: designing high-trust, high-impact workshops!
We unpack what the Chief of Staff role really entails, why the role has exploded in the growth-stage tech world, and how Harry discovered that the real value wasn’t in “doing it all,” but in helping leadership teams actually get aligned and make decisions that stick.
Harry shares why he’s betting big on workshops as the human antidote to AI overload—and how even non-tech companies are hungry for them. We also talk candidly about the limits of fractional Chief of Staff work and what it takes to design a portfolio career around the role.
If you’re considering the COS role or a founder craving a business strategy reset without another bloated offsite, this episode is for you!
Check out Harry’s work at one two growth

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