The Diary of a CFO

Lauren Pearl is a CFO, advisor, three-time founder, and educator who teaches financial modeling at NYU Stern's Berkeley Center for Entrepreneurship. A former software developer turned finance leader, she has helped more than 300 companies build a financial foundation to scale and currently serves as fractional strategic CFO at North Pole Security, focused on AI security for finance leaders. In this episode, Lauren shares the AI danger triangle framework: three conditions that, when combined, create serious risk for any finance team using AI tools. She explains why startup experience changes how CFOs approach risk, how she onboards into new organizations using a consulting-style diagnostic, and why experience and judgment will become the rarest, most valuable skills in finance as AI makes technical ability more accessible. She also tells the story of discovering her family business had to close after reading its financial statements for the first time at business school. Today's episode is sponsored by Lineos: bring your finance lifecycle into one line of sight, from planning to reporting. Learn more at lineos.com

Alex Curran is the CEO of Aptitude Software and has spent 20 years working with CFOs at some of the world's most complex finance organizations. In this episode, she shares why 87% of CFOs say AI matters but less than 10% can show a return, and what needs to change at the systems level before any AI strategy can deliver results. Alex breaks down the three conversations every CFO must have with their CEO, what it actually takes to get to a zero-day close, and why putting AI on top of legacy architecture makes the problem worse, not better. Today's episode is sponsored by Fynapse, an AI-native finance ERP. Learn more at fynapse.app

David Fubini spent 35 years as a senior partner at McKinsey & Company, where he co-founded the firm's global merger integration practice. He has advised on dozens of major transactions, including the deal that brought IBM's PC business to Lenovo. He started his career at Johnson & Johnson, where he was part of the team that launched Tylenol as a consumer brand. He now teaches at Harvard Business School and is the author of four books, including his latest, Post-Merger Integration, released in June 2026 with Wiley. In this conversation, David explains why most M&A deals fail, and why the answer has very little to do with the financial model. He breaks down the cultural and organizational blind spots that CFOs and management teams consistently miss during due diligence. He shares what happened behind the scenes of the IBM-Lenovo deal, including the moment that finally brought two very different teams together across 12 time zones. And he talks about what the best CFOs he has worked with do differently: they act as counselors, not disciplinarians. They speak hard truths to their CEOs. They translate numbers into what is actually happening inside the organization. Whether you are a CFO navigating a deal, a finance leader thinking about M&A strategy, or someone who wants to understand what really happens after the paperwork is signed, this episode will change how you think about integration.

In this solo episode of The Diary of a CFO, I sit down halfway through the year to reflect on what I’ve learned during my first two years in the CFO seat, as well as the lessons I’ve gathered from speaking with more than 40 CFOs on this podcast. I talk about the difference between strategic thinking and strategic leadership, and why most companies test for the first when the second is what ultimately keeps you in the seat. I also explore why your relationship with your CEO and board can be the single most important factor in whether you succeed or get pushed out, including a real story from a CFO whose CEO asked her to stop attending board meetings after she shared information he didn’t want disclosed. We get into why working with a founder CEO is completely different from working with a hired CEO, what that means for navigating the role, and how mid-market CFOs operate at different altitudes in the same day, from talking to funders to reviewing accounting entries. I also unpack what I mean by “strategic influence” and why it has to permeate everything you do and say as an executive, right down to the words you choose. And finally, I reflect on why alignment with your boss, your company, your family, and your health has become the one word that defines everything I’ve learned so far. This is not just for CFOs. If you’re in any senior leadership seat, this episode is for you.

Most ERP implementations do not fail because of the technology. They fail because of what happens before the system is even turned on. In this episode, I sit down with Sharon Barboza, Manager of Digital Services at Citrin Cooperman Advisors. Sharon is a licensed CPA who has worked on every side of finance, from public accounting to controller to senior NetSuite consultant. She has seen hundreds of growing businesses go through system implementations and knows exactly where they break. We break down the five most common reasons ERP implementations fail. Why accounting is always the last department brought into the conversation and what that costs in redesign and delays. The client who mentioned a Bulgarian subsidiary one week before go-live that nobody knew about. Why accountants resist leaving Excel and how to show them the value without making them feel replaceable. The 78-tab forecasting spreadsheet that took days to update and why that was the wake-up call. How to build a roadmap that plans for where the business is going, not just where it is now. What to look for in your chart of accounts before you realize you needed it. How one client went from a failed implementation with another partner to a successful launch by rebuilding trust from scratch. And how embedded banking tools like Fispan eliminated the constant cycle of broken bank feeds and manual file transfers. Whether you are a finance leader about to start an ERP implementation, in the middle of one that feels like it is going sideways, or still trying to decide if it is time to leave Excel, this episode covers the full picture. This episode is brought to you by FISPAN. Learn more at fispan.com.