Podcast · 39 min

When is it Time to Hire a CFO?

Steven Uster and Deepak Ramachandran (Cash Flow & Tell) · Cash Flow & Tell Free Intermediate

Two founders who built and scaled FundThrough talk through the same build-versus-outsource finance call you are weighing, and they are candid about the mistakes they made along the way. They walk through starting with a bookkeeper versus jumping to a CFO, fractional versus full-time, and the red flags that mean you waited too long. It is a starting point for hearing how the decision actually feels from the founder seat, not a template to copy exactly.

• The first finance hire is usually a bookkeeper, not a CFO. Treating finance as a cost center rather than a value generator is the mistake they call out most.
• There are real red flags that you have waited too long to bring in finance help, and messy investor or bank conversations are near the top of the list.
• Fractional finance leadership can bridge the gap before you can justify a full-time CFO salary.