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Chrissy O'Hara built her career the traditional way: audit at EY, a financial reporting role at Fannie Mae, time at the hedge fund Citadel, and an MBA earned at night. Then she helped build the accounting software she and her husband wished existed, and stepped into life as a startup CFO.
In the latest episode of the FEI Podcast, recorded live at the FEI Financial Leaders Forum in San Antonio, host Heather Cole sits down with O'Hara, CFO of SoftLedger, to talk about what happens when a finance leader trades a structured corporate path for the unstructured world of entrepreneurship.
From Fannie Mae to Founder
O'Hara's path started conventionally: George Washington University for undergrad and a master's in accounting, then EY, Fannie Mae, and Citadel, where she earned her MBA at Northwestern at night. Her husband, meanwhile, was frustrated by the state of mid-market accounting software and teamed up with a college friend, software engineer Jeff Ostrega, to build something better. What started as nights-and-weekends work eventually became SoftLedger, and O'Hara moved from moonlighting on the company's books to full-time CFO two years ago.
What Does Entrepreneurial “Freedom” Actually Look Like?
O'Hara is candid that outsiders tend to romanticize entrepreneurship as freedom without acknowledging the tradeoffs. The flexibility is real, she says, but so is the pressure: unpredictable cash flow, family members who ask when she and her husband are going to get real jobs, and the discomfort of not having a clean answer when a deal falls through. She recalls one particularly difficult stretch, navigating two acquisition processes at once while pregnant with her second child, only to watch one deal collapse.
Her advice for finance and accounting professionals weighing a similar leap: expect it to take longer than planned, expect setbacks, and build in the flexibility to pivot when the plan changes.
The Biggest Lesson: Letting Go of Perfection
O'Hara's accounting background, she says, taught her to cross every T and reconcile every penny. That instinct does not survive contact with a startup. She and Cole traded stories about the moment each of them let go of needing the books to balance exactly, and how liberating it felt to redirect that energy toward growth, sales, and the parts of the business that actually move the needle. Her advice for financial leaders making a similar transition: hold onto the rigor that makes finance professionals valuable, but learn which details can wait.
Where AI Fits In
O'Hara uses Claude and ChatGPT daily, largely for accounting research: pulling different interpretations of a technical question, comparing sources, and catching gaps that a single search would miss. SoftLedger has also built AI into the product itself, including support tools that let a single customer success hire do the work of a larger team. Internally, the company even has an AI assistant nicknamed Balance Buddy, modeled after her co-founder and built to answer day-to-day accounting questions over Slack.
The bigger point, O'Hara says, is one she has carried since SoftLedger's earliest days: accounting software should flex to fit how a business actually operates, not the other way around. She and Cole compared notes on the rigid, legacy ERP systems both had worked with earlier in their careers, and agreed that flexible, API-connected tools are finally catching up to that vision.
Her Message to Financial Leaders: Take More Risk
O'Hara closes with a challenge to the profession: more finance and accounting professionals need to become entrepreneurs, and more need to be in the room when new technology and tools are being built. Otherwise, she says, those decisions get made without them. It is a theme Cole returns to often in her coaching work: financial leaders who feel unheard usually are not in the room where the real decisions happen.
🎧 Listen to the full FEI Podcast episode »