“I look for someone who has done the exact next chapter the company is facing, because a CFO who only knows the stage behind you will slow you down. Then I test whether they can explain numbers to non-finance people and build trust fast, since the role is mostly people, not spreadsheets.”
“I look for someone who has actually operated a business, not just run models, because the CFO job is walking through messy trade-offs, not turning spreadsheets into graphs. Before you go strategic, make sure your books are clean and real-time; a CFO can't do their work on bad data.”
“I spent 14 years as a CFO, and the best ones I hired or worked alongside had a superpower beyond the job description, usually fundraising or deal-making, because most startups burn cash and need someone who loves that game.”
“I see too many founders hire a CFO when what they really need first is clean data, a working model, and someone who can explain the numbers to the board. Start there, then look for a CFO who has actually raised capital in your stage and industry, not just run accounting teams.”
“I look for someone who can be a vocal financial advocate inside the business, not just a strong operator behind the desk. At Under Armour, the first finance people I embedded were a little more extroverted than typical, because they had to win over skeptical business partners before the function could scale.”
“Hire the person who can sit across from you and explain why your cash flow matters more than your P&L, because when that investor calls, that's the CFO who keeps you funded. I learned that parachuting into PE-backed businesses; the ones who scaled had finance leaders who made the numbers tell the story before anyone asked.”
“I’d give them a real scenario your business is facing and ask them to walk me through how they’d tackle it, not the solution, just the approach. That’s where you see whether they actually think like a CFO or just produce pretty reports.”
“The best CFO I hired was the one who asked me harder questions than the board did, not the one with the shiniest resume. I look for someone who has rebuilt reporting nobody trusted and can show me exactly how the numbers change a decision before I make it.”