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
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