In this episode, CJ interviews Jeff Cassidy, CFO of Prodigy Education about navigating a diverse career across multiple industries and building strong teams based on ambition and skills rather than credentials. Having worked in financial services, biotech, restaurants, travel, edtech, and even crypto, Jeff shares the story of his own varied career, giving advice on finding the “right” career path, achieving personal product market fit, and what he looks for in a new role. He talks about how he goes about building a strong team and the qualities he looks for in applicants, while sharing stories of some of the hiring choices he’s made. The conversation touches on the evolving landscape of higher education, the failures of American four-year colleges, and the need for more practical skills and diverse experiences. Jeff also discusses the challenges of leading a travel company through the COVID-19 pandemic, highlighting the importance of transparency, customer empathy, and supplier management.
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SPONSORS:
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RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. Whether it's multi-element arrangements, subscription renewals, or complex usage-based contracts, RightRev takes care of it all. That means fewer spreadsheets, fewer errors, and more time for your team to focus on growth. For modern revenue recognition simplified, visit rightrev.com and schedule a demo.
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TIMESTAMPS:
(00:00) Preview and Intro
(03:28) Sponsor – Brex | Planful
(06:48) Finding Personal Product Market Fit
(12:13) Qualities to Look for in a New Role
(14:01) The Misconception About Finding the “Right” Career Path
(16:04) Sponsor – Vanta | RightRev
(18:32) Linear and Non-Linear Career Moves
(20:16) Hiring Based on Ambition and Skills
(22:38) How American Four-Year Colleges Are Failing
(29:20) Transitioning into Finance
(32:05) The Story of a Surprising Finance Hire
(35:20) Lessons from an Applicant’s Interview Fail
(38:16) Running a Travel Company in the Pandemic
(41:45) Supplier Management in a Crisis
(43:59) Lessons on Communicating Internally
(45:43) Long-Ass Lightning Round: An Early Career Mistake
(48:25) Advice to Younger Self: Pursue Interests
(49:28) Finance Software Stack
(49:59) Craziest Expense Story
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