From CPA to Founder: Why This CFO Says It's Time to Take More Risk – with Chrissy O'Hara

About this Episode

What happens when a CFO trades the structure of a traditional corporate finance career for the unpredictability of a startup? In this episode, recorded live at FEI's Financial Leaders Forum in San Antonio, host Heather Cole sits down with Chrissy O'Hara, CFO of SoftLedger, to talk about the real tradeoffs of entrepreneurial freedom: cash flow stress, family members who keep asking when the “real job” is coming, and the discipline it takes to keep pivoting when plans change. O'Hara also shares how she learned to let go of the perfectionism her CPA training instilled, how she and her team use AI tools like Claude and ChatGPT day to day, and why she believes more finance and accounting professionals need to step into entrepreneurship and be in the room shaping the next generation of tools, rather than waiting for someone else to make those decisions for them.