Startups don’t need spreadsheet CFOs—they need operators who can think like owners.

That’s the core message in this episode of The Growth-Minded CFO as hosts Alex Louisy (CEO, Upflow) and Lauren Pearl sit down with Jon Gross, CFO of RepeatMD.

In this conversation you’ll learn:

👉 “Three-level CFO” playbook – how Jon shifts from board-level strategy to ground-floor execution without missing a beat.

👉 Why empathy for sales, product & customers is a super-power for finance leaders.

👉 The art of balancing professionalising a business without killing the scrappy magic that made it special.

👉 How your cap-table incentives should shape growth targets and risk tolerance.

👉 Jon’s method for carving out time to write, share and build in public—and why more CFOs should do it

👉 Practical tips for turning finance into an enablement function (not the department of “no”)

About our guest: Jon Gross is CFO at RepeatMD, a Houston-based SaaS platform helping aesthetics, med-spa and wellness clinics drive repeat business through rewards and financing tools. A former investment banker, PE operator and chief-of-staff, Jon brings rare range—from capital markets to zero-to-one execution.

Connect with Jon ➡️ https://www.linkedin.com/in/jon-gross10/

Connect with Alex ➡️ https://www.linkedin.com/in/alexlouisy/

Connect with Lauren ➡️ https://www.linkedin.com/in/laurenepearl/

• 00:00 Intro & the “operator” mindset

• 03:10 What a “three-level CFO” really does
• 09:15 From spreadsheets to real-world execution
• 14:40 Wearing multiple hats without losing focus
• 23:30 Risk-taking in a CFO seat (NetSuite, AI & more)
• 28:05 Partnering with founders: enabling, not blocking
• 32:15 Why CFOs should write and share publicly
• 36:40 Rapid-fire: habits, inspiration & growth hacks

• 38:30 Wrap-up & how to subscribe

Watch the full video version of this episode on YouTube: https://youtu.be/bmHXjDPnQe0?si=bODFdQU02rsQnTbz

The Growth-Minded CFO podcast aims to challenge the status-quo and explore how the best CFOs approach their work and lives. Hosts Lauren Pearl (Fractional CFO, 3-time Founder and Startup Finance Instructor at NYU) and Alex Louisy (FinTech CEO and Y Combinator graduate) speak with inspiring finance and business leaders who’ll share what great CFOs are doing to support high-performing organizations.

This podcast is powered by Upflow - a Financial Relationship Management platform enabling faster payments, stronger customer relationships and efficient growth for your business.

Join thousands of next-level finance leaders and go from chasing invoices to engaging customers. Find out more at ⁠⁠upflow.io

Want to get in touch? Reach out to our producer at joseph.sweeney@upflow.io