From Banker to Builder: Hands-On CFO Lessons for SaaS, with Jon Gross
When Jon Gross swapped his investment banking spreadsheets for startup life, he didn’t just change jobs—he learned to change altitudes on demand.
In this episode of The Growth-Minded CFO podcast, hosts Alex Louisy and Lauren Pearl dig into how the CFO of RepeatMD jumps from board strategy to hands-on ops without missing a beat.
Below is a friendly recap of the big ideas (and the exact words Jon used to drive them home).
What’s a “Three-Level CFO”?
Jon borrows a basketball analogy: a great scorer finishes at the rim, in mid-range, and beyond the arc. For finance:
“You could be having a board-level conversation around how to capitalize this business… We could be leading a project, galvanizing a team… and the ground level is doing the work—maybe I'm building the budget model, maybe it's hands-on-keyboard work to make sure that work gets done right.”
The takeaway? Early-stage companies need finance leaders who can switch altitude—fast.
From Spreadsheets to Real-World Execution
Numbers look neat in Excel, but Jon says the hidden cost is time:
“The translation of spreadsheet to reality—how long things take, how a number on a spreadsheet compares to the cost of implementing that, the people cost.”
His cure: sit with sales, run the drip campaigns yourself, and budget for the grinding months behind every “quick win.”
Risk-Taking in the CFO Seat (NetSuite, AI & More)
Rolling out NetSuite and experimenting with finance-team AI felt bold, but Jon checks risk against the shareholder map:
“It depends on the incentives of the people on your cap table… the incentive for a PE-backed company may be ‘give me 10 % growth for the next five years.’ A VC fund may say ‘I need you to grow 200 % year over year for me to make that happen.’”
Line up the tech bets with those expectations and the finance team becomes the accelerator, not the brake.
Partnering with Founders: Enable, Don’t Block
RepeatMD’s CEO is a “master marketer,” so Jon bakes flexibility into the budget:
“G&A is an enablement function… how do I enable the superpowers our founder has and not restrict that? … There's maybe a creativity budget that's in our marketing budget that we put in there as a cushion.”
Translation: give great ideas a runway, then trim elsewhere instead of killing the spark.
Why CFOs Should Write in Public
Jon’s LinkedIn posts began as an exercise in clearer communication:
“It actually started as more of a personal-development experiment… rip the Band-Aid off and just go do it.”
He treats writing like gym reps—some weeks zero, some weeks two—as long as the habit moves forward.
The Growth-Minded Mantra
“If you're not uncomfortable, you're not growing.”
Whether it’s swapping spreadsheets for street-level ops or piloting AI agents, Jon’s playbook is simple: keep changing altitude and stay a little uncomfortable.
Full Episode
If Jon’s journey sparked an idea—maybe a “creativity budget” or a writing habit—pass this article to a finance friend who’s ready to think beyond the spreadsheet.
Listen (and subscribe) on Spotify