The CFO of Upwork answers every CFO’s most burning question

Coworking is a recurring segment where we talk with CFOs and other leaders in the finance space about their experiences, their companies, and the larger economy. Let us know if you are—or you know—a CFO we should interview.

While Erica Gessert, the CFO of Upwork, has been on the finance teams of some big household name brands including PayPal and Sprint, this is her first time in the CFO chair.

Gessert describes herself as an operational CFO, who oversees everything “end to end, from product and production to delivery, adoption, and financial outcomes.”

CFO Brew asked her about prioritizing revenue streams, preparing for a possible recession, and how AI is impacting her industry.

How is being the CFO of Upwork different or similar to your role at PayPal?

One of the things that attracted me to Upwork from PayPal is that they are two-sided networks. Upwork’s a marketplace. PayPal is what we call a network, but it has two sides: merchant and consumer. [At Upwork], it’s client and knowledge worker or talent. That’s where the similarities end.

Learning the human capital industry, the management of all these diverse types of work and the talent that goes with it, and really understanding clients’ needs that they’re assessing hiring is a totally different industry than payments. I thought payments was complex. But the complexity of enabling work and the hiring process…is even more complex in many ways.

How do you decide which revenue streams to prioritize?

Every single company I’ve ever been at, the most impassioned conversations are around prioritization…We knew that we needed to increase our profitability, not just to gain investor confidence and to show profitability, but also so that we could enrich our balance sheet and allow ourselves the capacity to be able to invest and actually acquire companies where we saw gaps in our roadmap.

How has AI been affecting your business?

AI was a huge overhang for our valuation, quite frankly…There was this belief that all work was going to go away. AI was going to take it, and especially work that’s done by people like freelancers, because they are impermanent…Actually, the opposite is true. So one of the things that we really thought hard about was, how do we use AI to accelerate our business to really, truly become a growth lever, which it is for us now? And we’ve done that in two ways. One is an injection of AI-enhanced experiences into the platform. If you think about the hiring process and just how friction filled it is…now, all of that is done by AI, basically 100% end to end. Uma, which is Upwork’s Mindful AI, our AI companion, writes the job posts. It can also write the proposals from the freelancers. It can review proposals for the client. It can help to curate the proposals that are written. It can actually conduct interviews and also, coming soon, we’re starting to inject more agentic qualities…But the second way is really the growth of the AI category itself, so the AI job category on our platform, that’s really taking off for us.

We are in an era of uncertainty and possible recession. How does that impact your role as CFO?

What I’ve been doing, along with my [CEO] and the rest of the management team, is really working on strategies that make us macro-agnostic. We work in an industry that is heavily influenced by macroeconomic impacts, the staffing industry…We’ve been gaining share. The ways we’re doing that are…identifying new revenue streams for ourselves that can grow regardless of macro conditions. Some of those are like subscription products for freelancers. The other thing that we’re doing is really deploying our analytics heft to create variable pricing on our platform according to the dynamics of supply and demand on the platform...It’s enabling us to have these growth revenue streams, both in volume and revenue, during this time.