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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Ready to discover how to hire for potential rather than past credentials—and why it could transform your business?
In this episode of Parallel Entrepreneur, Mark Cleveland sits down with Caitlin MacGregor, CEO and Co-Founder of Plum, to talk about building a high-growth company while raising a family and defying the usual startup playbook.
If you’re juggling multiple ventures—or planning to—Caitlin’s journey will inspire you to embrace change, experiment with collaboration, and double down on what really drives success.
Highlights:
- Power Couple: Why being married to her co-founder is Caitlin’s superpower (despite investor skepticism).
- 13 Years of Growth: Balancing fundraising with customer-driven revenue, and why sales might matter more than venture capital.
- People Over Résumés: How Plum’s behavioral data approach uncovers “diamonds in the rough” for any role.
- Authentic Leadership: Leading with love, care, and collaboration to break down silos and foster real engagement.
- GenAI & the Future: Why tasks, not jobs, are being automated—and how to reinvent your organization for exponential success.
Don’t miss these candid insights from a founder who’s rewriting the rules on entrepreneurship and talent strategy.
Show Notes:
- Plum, a revolutionary talent platform - https://www.plum.io/
- EY Entrepreneurial Winning Women - https://www.ey.com/en_us/entrepreneurial-winning-women-north-america/class-of-2024
- Blitzscaling: The Lightning-Fast Path to Building Massively Valuable Companies by Reid Hoffman - https://www.blitzscaling.com/
- Bo Burlingham - https://boburlingham.com/
- The Revenue Engine: Fueling a B2B High Octane Pipeline by Kara Smith Brown - https://therevenueengine.com/
- The Fourth Wing by Rebecca Yarros - https://rebeccayarros.com/fourthwing
About Plum:
Dive into a fresh take on talent strategy with Plum, the durable skills company. Our robust talent assessment platform, PlumThrive, helps you harness the lasting impact of the core competencies that matter. By focusing on durable skills, we transform your company into a skills-based powerhouse, allowing you to make better talent decisions across the employee journey.
Are you ready to boost your hiring precision and extend employee tenure? Explore PlumThrive and transform your workforce strategy today: https://www.plum.io/book-demo
23 episodes
