How Caitlin MacGregor is Unlocking Human Potential with Plum.io
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.
Chapters List:
00:00:56 Meet Caitlin MacGregor: Founder, CEO & Human Potential Champion
00:02:44 When Your Co-Founder Is Your Spouse
00:05:08 Growing a Family & a Company Simultaneously
00:09:21 Fundraising Lessons: 99 No’s for 1 Yes
00:15:17 Rethinking Growth in a Shifting Market
00:17:30 Why Sales Might Matter More Than Fundraising
00:20:48 Integrating Feminine Dimensions of Leadership
00:25:16 Symbiotic Health - the New Model for Business Success
00:26:51 Well-being, Mindfulness & Self-Awareness
00:31:06 The Science of Unlocking Human Potential
00:35:00 Hire for Behaviors, Not Resumes
00:35:57 The Collaborative Operating System: Eliminating Silos
00:38:48 Perfection vs Collaborative Creation
00:45:42 Transforming Company Culture to Eliminate Politics
00:48:00 A Hiring Experiment That Sparked Plum
00:52:18 Advice for Future Generations
00:57:07 GenAI & the Future of Work
00:59:55 Books, Escapes & Art
01:04:53 The Future of Change Management
Show Notes:
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.
Chapters List:
00:00:56 Meet Caitlin MacGregor: Founder, CEO & Human Potential Champion
00:02:44 When Your Co-Founder Is Your Spouse
00:05:08 Growing a Family & a Company Simultaneously
00:09:21 Fundraising Lessons: 99 No’s for 1 Yes
00:15:17 Rethinking Growth in a Shifting Market
00:17:30 Why Sales Might Matter More Than Fundraising
00:20:48 Integrating Feminine Dimensions of Leadership
00:25:16 Symbiotic Health - the New Model for Business Success
00:26:51 Well-being, Mindfulness & Self-Awareness
00:31:06 The Science of Unlocking Human Potential
00:35:00 Hire for Behaviors, Not Resumes
00:35:57 The Collaborative Operating System: Eliminating Silos
00:38:48 Perfection vs Collaborative Creation
00:45:42 Transforming Company Culture to Eliminate Politics
00:48:00 A Hiring Experiment That Sparked Plum
00:52:18 Advice for Future Generations
00:57:07 GenAI & the Future of Work
00:59:55 Books, Escapes & Art
01:04:53 The Future of Change Management
Show Notes:
- Share and engage with this interview on LinkedIn: https://bit.ly/3FKdXQF
- 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
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
