The Culture Shift After Series A

What do you do when you’re suddenly in charge… and totally unprepared?

In this episode, I speak with Gillian Davis, leadership strategist and founder of Overtime Leader, who’s spent the last decade helping scaleups grow their leadership and culture as they move from scrappy startup to mature company.

Gillian’s journey started with crisis: she took over her family’s business when her father fell ill. She later left corporate “with a vengeance,” and found herself dropped into a high-growth tech company with zero systems, zero onboarding, and a ton to figure out.

Since then, she’s served as VP of People at WeTransfer, co-authored the book First-Time Leader with George Bradt, and worked with leadership teams to help them scale intentionally — before chaos sets in.

In this conversation, we talk about:

* The intern confrontation that reshaped her leadership style

* Why she quit corporate without a plan — and what she found instead

* How product thinking changed how she does organisational design

* Common mistakes founders make when hiring senior leaders

* Why fast growth doesn’t mean rushing leadership

Whether you’re a founder, a first-time VP, or just someone trying to lead through uncertainty — this one’s packed with stories and insights you’ll want to remember.

🔗 Guest Links

* Gillian’s website: OvertimeLeader.com

* Gillian on LinkedIn: linkedin.com/in/davisgillian

* Her book: First-Time Leader (with George Bradt)

🗂️ Timestamps

* 00:00 – Intro & Gillian’s origin story

* 05:30 – Leading through crisis with no playbook

* 15:00 – The intern confrontation that changed everything

* 22:00 – Leaving corporate with no plan

* 26:00 – Joining a tech startup with no systems

* 32:00 – Product thinking meets leadership

* 45:00 – Helping founders build leadership post-Series A

* 59:00 – The importance of brave, long-term leadership

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit scaleupleaders.substack.com