Greatest Hits: Building Leadership Through Community

In this Greatest Hits episode of CFO Weekly, Mark Dempster, Founder at The Circle by Founders Circle Capital, joins Megan Weis to explore why peer communities are essential to CFO leadership. Drawing on his experience building The Circle and supporting finance executives at venture-backed companies, Mark shares how vulnerability, peer support, and leadership development help CFOs navigate pre-IPO pressures and prepare for the demands of public company leadership.

Strong CFO leadership isn't built on financial expertise alone. It also requires the ability to navigate uncertainty, influence people across the organisation, and learn from others who understand the pressures of the role.

In this Greatest Hits episode of CFO Weekly, Megan Weis speaks with Mark Dempster, Founder at The Circle by Founders Circle Capital, about the importance of peer communities for CFOs navigating the demands of pre-IPO growth.

Drawing on his experience at the intersection of leadership, brand, and venture capital, including his time as a marketing partner at Sequoia Capital, Mark shares how The Circle evolved from informal CFO dinner conversations into a structured peer community supporting finance leaders at venture-backed companies.

He explores why CFOs need trusted spaces to share challenges, embrace vulnerability, and develop the leadership capabilities required to take their companies through the IPO journey.

Whether you're preparing for an IPO or looking to become a more effective finance leader, this episode offers valuable perspectives on building confidence, strengthening relationships, and scaling yourself alongside your company.

What You'll Learn:

Why CFOs in the IPO tractor beam face constant reinterviewing by their boards
How vulnerability and peer support combat the isolation inherent in the CFO role
The critical shift from individual contributor to leader and storyteller
Why the CFO role has the highest unfilled recruiting rate in venture capital
How community infrastructure helps CFOs avoid replacement at the IPO threshold
The power of lived experience over data alone in high-stakes decision-making

Learn more about Mark:

Mark Dempster on LinkedIn
The Circle by Founders Circle Capital Website

Episode resources:

Personiv's Website
Personiv on LinkedIn
Personiv on Facebook
Personiv on Twitter

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Previous guests include: Tom McDermott, CFO at Career Certified, Claire Bramley, CFO at Teradata, Chris Miles, Founder of Money Ripples, Ranil DeSilva, CFO & COO at CARE, Jordan Grumet, Financial Independence Expert & Host of Earn & Invest & William Washington, Global CFO at Baker McKenzie

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