Finance Ops Leadership in a Digital World

Amartya Singh: Welcome to Inside the CFO Office. Today’s guest is Jason Wooten, Head of Finance Operations at ClickUp. His journey is anything but traditional — starting in cold-calling sales before moving into finance leadership roles spanning collections, procurement, deal desk, and revenue operations.

Jason Wooten: I started in BDR roles — literally cold-calling from a printed directory. That experience taught me resilience, focus, and execution, which I carried with me across roles. As I moved into operations and eventually into finance, I found myself always collaborating with finance teams. The transition felt natural.

Amartya: One of your toughest and most rewarding experiences was in cash collections. What stood out?

Jason: Cash collections is all about cross-functional collaboration. The biggest mistake companies make is treating it as a silo. To do it well, you need deep context from sales, customer success, and service teams. Most disputes aren’t about money — they’re about product gaps, unmet expectations, or poor communication. You can’t solve those without understanding the full customer journey.

Amartya: That’s a powerful insight — balancing logo vs. cash retention is always tough. You also led a major office relocation. Tell us more.

Jason: That was a 2-year project — finding off-market space, negotiating the lease, securing government incentives, and overseeing construction. I had zero experience in real estate or project management. It was overwhelming, but transformative. My biggest learning? Say yes to the rocket ship, even if you’re not sure which seat you’re in.

Amartya: Let’s talk about transformation. Any standout projects?

Jason: At Cvent, we launched a customer payment processing solution. Initially simple, but as scale increased, the cracks showed. Years later, we had to completely rebuild it — and more importantly, rethink how finance engages with customers. Finance is usually not seen as customer-facing, but when it comes to money, perception matters. This transformation changed how both customers and internal teams viewed the finance function.

Amartya: Speaking of change — what’s your view on the current CFO tech landscape?

Jason: It’s outdated. Finance systems are sticky, underinvested, and stale. There’s a huge gap between platforms and point solutions. No one’s building an intelligent, connected platform that uses AI meaningfully across finance. AI vendors either solve tiny problems or provide clunky models that are hard to price and even harder to forecast. Legal risk and pricing complexity slow down adoption in bigger companies.

Amartya: Totally agree — the future is connected data and agentic AI across finance workflows. Final question — what advice do you have for aspiring finance leaders?

Jason: First, lead yourself. Know your motivations, take care of your health and routines. Second, own your career. No one else is responsible for your growth. Third, prioritize people. Every business problem has a people dimension — finance leaders can’t ignore that. And finally, raise your hand for big, uncomfortable challenges. That’s where real growth happens.