Troy Anderson is CFO of Kelly Services, a staffing solutions provider to various industries, who has spent his career driving transformation across some of the most complex business environments. Before joining Kelly, he served as CFO at Universal Technical Institute, where he helped double revenue over five years through a mix of organic growth and strategic acquisitions. Earlier in his career, he held senior finance leadership roles at Conduent, a $6billion player (bought by Xerox). 

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Stephen Hedlund is head of finance at Rillet, an AI-native ERP which has raised over $100million from Sequoia and  Andreessen Horowitz. In  Steven’s words Rillet is “building the modern NetSuite.”

“To succeed, planning alone is insufficient. One must improvise as well.”

Eddie Reynolds, CEO of UnionSquare Consulting, opens up about the often-fraught relationship between CFOs and CROs. Eddie shares insights from his unique journey—from banking and private equity to being an account executive at Salesforce which forecast within 5% accuracy despite 30%+ growth.

The conversation tackles the critical disconnect between finance and go-to-market teams: Why do CFOs struggle to trust CRM pipelines? What breaks when companies hit $50-100M in revenue? 

In this episode:

Bobby Bray brings his perspective from more than 20 years in banking and consulting with Capital One, Oliver Wyman, and Regions Bank. The retired Navy Captain with four commands talks about strategic decision-making under pressure, working with Fortune 150 C-Suite executives, and the rigor required in FP&A.

He says: “To use an aviation term you need to be able to follow the drop of gas through the engine and understand the different cogs in the engine that turns a drop of gas into thrust, but it also is what turns raw data into usable analytics on the back end.”

Five-time CFO Rick Smith has led finance at companies including inVentiv Health Communications, Exos, Parchment, Solera Health before founding Bonfire advisory. He is also the author o fDemystifying the Role of the CFO in Venture and Growth Stage Companies, a no-nonsense approach to the topic. Reviews for the book include: “This book is a must-read if you want to understand how to scale a company as a CFO” and “Should be required reading for CEOs and PE people along with CFOs.”

In this episode Smith provides his take on being a CFO and his long background in FP&A, providing insights on:

Link to the book: Demystifying the Role of the CFO in Venture and Growth Stage Companies

Preston Naegle started his career in private equity at Leavitt Equity Partners (founded by Michael Leavitt, the former U.S. Secretary of Health and Human Services. Negale then moved into the operating world and for more than 2 years has led strategic finance and FP&A at a PE-backed Midway Mechanical Services  in the HVAC (Heating, Ventilation, and Air Conditioning) industry at the company which has completed 15 acquisitions (3 in 2025 alone) within the mechanical, electrical, and plumbing sector across the Western US region. 

In this episode

Glenn reconnects with Adam Shilton—who reveals the highs and lows of more than a decade selling to finance teams and what 134 deals in 36 months taught him about CFO challenges. The founder, writer, and speaker has now launched his own venture focused on helping entrepreneurs and solo business owners.

What does it take to be the finance leader behind Hollywood stories? Diya Sagar, CFO of AWA Studios, which produces critically acclaimed, original stories for comics, TV, and movies, joins Glenn Hopper to reveal how she manages the money behind the magic—from funding graphic novels that may not pay off for years to navigating the unpredictable world of graphic novels, film and TV deals. 

With more than 20 years of experience helping startups scale from seed to series B, Maria Azatyan has built architectures for companies across ai, robotics and the new space economy, translating complex technologies into numbers. This is coupled with her frank perspective as a single mother balancing finance leadership and advising startups. 

Joyce Li, CEO, and chief AI strategist at Averanda Partners, brings a rare combination: CFA charter holder, computer science graduate, MBA from Wharton, Board advisor on AI. She advises on multi-billion dollar investment strategies and works with boards and C-suites on AI strategy, governance, and adoption.