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.” In this episode:

• How Isaac Asimov’s Foundation helped me discover finance
• Experience from enterprise at Walmart to building startups
• Go-to-market (marketing) to Head of Finance Gillet
• The moat for leading ERPs and our strategy
• Being the ICP and marketing voice for Rillet

“To succeed, planning alone is insufficient. One must improvise as well.” ― Isaac Asimov, Foundation

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:

• How Salesforce was able to forecast with 5% accuracy,
• The role of FP&A and CROs in go to market strategy and efficiency
• The issues with LTV to CAC ratio in SaaS
• Biggest challenges of the CFO/CRO relationship
• Bottoms up annual planning working with finance

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.” In this episode

• A Truly Non-Traditional Path to Finance
• Commercial banking as the most educational finance job
• Discipline and rigor in FP&A
• Cloud infrastructure changes in the past 7 years
• The rigor of a capital market stress test
• Explainability of AI in finance