Unconventional Career Insights from a CFO

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:

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Brex makes it easy to control spend before it happens, automate annoying tasks, and optimize your finances. Find out how Brex can help you make every dollar count at brex.com/metrics. 

Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics.

Vanta's trust management platform takes the manual work out of your security and compliance process and replaces it with continuous automation. Over 9000 businesses use it to automate compliance needs across over 35 frameworks like SOC 2 and ISO 27001. Centralize security workflows, complete questionnaires up to five times faster, and proactively manage vendor risk. For a limited time, get $1,000 off of Vanta at vanta.com/metrics. 

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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FOLLOW US ON X:

@cjgustafson222 (CJ)

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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