In this episode James Kennedy sits down with Chris May, founder and CEO of Quadrant Advisory, to explore what separates real CFO strategy from everyday accounting. From turning around a $50M political consulting firm to navigating tricky incumbent finance teams, Chris shares practical advice for business leaders and fractional CFOs alike.
Together, they unpack key finance tools like sensitivity analysis, working capital management, and how to tell whether your books are just “done” – or actually useful. Chris also walks us through his own acquisition of a bookkeeping SaaS and what it taught him about keeping services laser-focused.
Stick around to hear how Chris defines a great CFO – and why Naval Ravikant is his go-to business hero.
About Chris May:
Chris May is the founder and CEO of Quadrant Advisory, a U.S.-based fractional CFO and outsourced accounting firm serving growth-stage companies between $5M–$50M in revenue. With roots in Washington, D.C., Chris and his team specialize in professionalizing finance functions, uncovering strategic insights, and stepping in when founders realize they’ve outgrown their bookkeeping setup.
He’s also the co-owner of Less Accounting, a bookkeeping SaaS and service firm focused on simplifying accounting for early-stage entrepreneurs.
What You’ll Learn:
- Accounting vs. CFO Thinking: What makes a great fractional CFO – and how to avoid paying for “strategy” that’s really just back-office clean-up.
- Working Capital Mastery: How Chris helped one client free up $5M (yes, five million) by cleaning up their accounting and resetting the foundation.
- Sensitivity Analysis Simplified: What it is, why it matters, and how the best CFOs use it to shape better business decisions.
- Acquisition Lessons from the Trenches: Why Chris bought a small SaaS bookkeeping firm – and what worked (and didn’t) from the deal.
Episode Highlights:
- “If you’re not learning something new from your CFO every quarter, that’s a red flag.”
- “A real CFO helps you make decisions. It’s not just about clean books – it’s about actionable insights.”
- “Sometimes, the job is part-detective, part-diplomat. Especially when there’s an incumbent team and messy numbers.”
- “We paid 4x for the software side and 1x for services. Blended together, it was a fair deal – but the synergy is still a work in progress.”
More about Chris’s Role:
As CEO of Quadrant Advisory, Chris leads a team of nearly 30 remote finance professionals who act as fractional CFOs, controllers, and accounting experts for growth-stage businesses across the U.S.
Whether it’s untangling legacy bookkeeping, advising boards, or helping companies get acquisition-ready, Quadrant focuses on building scalable financial infrastructure. Chris is also a passionate advocate of clear, jargon-free finance communication – and believes that the best CFOs can explain complex models to a five-year-old.
