Durable Growth of the World’s Work Marketplace: A Q&A With Upwork’s Chief Financial Officer Erica Gessert

No company can run efficiently and effectively without a strong finance organization. Earlier this year, we at Upwork were thrilled to welcome Erica Gessert as our CFO to chart the course for our finance team, business growth, and investor community.

Erica joined Upwork following eight years at PayPal, where she ran strategic and operational finance as the firm’s senior vice president of finance & analytics and chief transformation officer. Previously, she worked in the telecom industry, including stints in finance leadership positions at Sprint and Virgin Mobile USA.

We spoke with Erica about her decision to join Upwork, how she is thinking about our opportunities for growth, and her advice for CFO peers and other finance leaders as they navigate uncertain macroeconomic times.

What spurred your decision to join Upwork?

There were three key things that drew me to join Upwork: the mission, the leadership team, and the power and strong growth prospects of two-sided marketplaces.

First, Upwork’s mission to create economic opportunities so people can have better lives really spoke to me. I’ve long been a passionate advocate for human rights, dignity and equality for all, and creating economic opportunity around the world fits right into that personal ethos.

At PayPal, I was the executive sponsor of the company’s engagement with The NXT Chapter, a non-profit that helps formerly incarcerated individuals reintegrate into their community and find new opportunities for success through job training. In the future, I hope to bring similar programs to Upwork.

Second, from the beginning, I’ve been impressed by our executive leadership team, with Hayden at the helm. And it’s not just the official leadership team; I’ve been greatly inspired by the deep leadership bench across all disciplines at Upwork. It’s an exceptionally smart, driven group of people who want to get things done. Together, I’m confident we can take this business to the next level.

And lastly, I was attracted to the strength of the two-sided marketplace that Upwork has built. Coming from PayPal, which is a two-sided network of consumers and merchants, I saw many parallels with Upwork’s business model that serves both clients and professionals. These networks are incredibly difficult to build, and even harder to disrupt.

Upwork is the market leader in our space, and the beauty is that we still have a huge amount of growth potential ahead. There was already legitimate strength in the business when I arrived, and I envision near-limitless potential for where we can go in continuing to build our value proposition for both clients and talent.

What’s your key focus as Upwork’s chief financial officer?

To put it simply, I’ll use a phrase that the team has heard from me early and often: durable, profitable growth.

In this day and age, when the “grow at all costs” mentality has dwindled in the tech industry and has been widely replaced by goals that lean into profitability, I am convinced Upwork has significant opportunities to grow our business profitably.

This is a naturally profitable business, and we are able to be profitable while still investing in growth. In our most recent quarter, we more than doubled our best-ever prior profitability outlook and raised revenue guidance for the year—that’s an immediate example of profitable growth that we now need to maintain and make durable.

That responsible growth will, in turn, allow us to invest more back into our customers. And we are doing just that. In Q2 of this year, we also grew our investment in research and development by 24% year-over-year. We are making and will continue to make meaningful investments in our customer experience.

Our perennial focus as an Upwork management team is on innovation, cost discipline, and identifying the investments with the highest ROI to generate profitable growth and shareholder value.

As we approach the end of 2023, what advice do you have for companies planning for the year ahead?

For our client companies who are planning for next year, I encourage my colleagues working with their business partners to really assess how they can most efficiently get work done. In periods of heavy cost reductions—like the past few quarters we just went through—there are always latent projects that don’t get done. As finance leaders work on planning and budgeting, there are a couple of crucial questions I’d encourage them to examine with their business partners:

1. Where do you have talent or skills gaps that will slow down or altogether block your strategic initiatives? How can we partner to solve and fill those gaps?
2. Are there places where focusing your team’s efforts on fewer things will make them better? Do you have systems, processes or organizational inefficiencies that are holding you back?

The key to growing profitably is ensuring that you do not reduce spend just for the sake of it, but rather look at the drive toward profitability as a catalyst for continuous improvement. Necessity is the mother of invention!

What should finance leaders know about Upwork and our work marketplace that could help them navigate this uncertain macroenvironment?

Finance leaders are expected to play a truly multi-faceted role within the companies they serve. They are stewards who ensure compliance and controls; catalysts who increase organizational effectiveness; strategists who enhance the company’s performance; and operators who drive efficiency across the business. Upwork can deliver against every one of these dimensions.

In supporting finance leaders with their steward or controller hats on, Upwork Enterprise Suite has compliance capabilities and classification services, as well as features like customized approval flows, that can provide finance pros with governance, control and peace of mind.

When it comes to finance leaders as catalysts looking to impact effectiveness of execution, speed to hire is their best friend. You simply cannot execute without the right people in the right positions at the right moments, and Upwork can help hire independent professionals in three days or less. Finance leaders acting as operators can derive significant cost savings and optionality by building out contingent workforces.

And for the all-important strategist role within finance, Upwork brings unparalleled workforce flexibility to scale up, scale down, resource growth projects, supplement teams with specialized skill sets, and enhance business performance.

The last thing I’d hope that finance leaders recognize is that embracing an alternative workforce is a real, low-risk approach to growth. Especially compared to the all-in cost of hiring FTEs and the huge cost of attrition, both to the bottom line and to productivity.

So many CFOs have recently been faced with the difficult decision to dramatically cut back headcount in response to macroeconomic factors. These decisions are painful and it doesn’t have to be that way. Having a more flexible workforce can enable execution and remove risk from the system at the same time.

Where do you think finance teams themselves have an opportunity to hire independent talent?

Companies of all sizes use independent finance professionals. I can confidently say every large enterprise uses independent finance professionals in several disciplines and it’s also extremely common at SMBs and start-ups. Companies use independent professionals in accounting, tax, financial planning & analysis, analytics, business intelligence and more.

When companies are in high-growth mode early in their life cycles, they’re often still getting their core processes up and running. Even just having a freelance expert adept at handling accounts receivable and accounts payable, for instance, can help them grow and scale.

What is the most recent role your team hired for on the Upwork platform?

We’re hiring people on the Upwork platform all the time. This quarter alone, we’ve hired a handful of independent professionals to support our finance team, including a tax technology analyst, product analysts, and a project manager for finance systems.

We continue to experience firsthand the competitive edge that the world’s best independent talent have given us in driving new levels of productivity, speed and growth.

Lightning round! What do you like to do in your free time?

This might be surprising, given my professional life revolves around numbers, but I’m an avid reader, both literature and non-fiction. I recently read a bit of a hybrid – a fictionalized account of the siege of Leningrad called “City of Thieves” by David Benioff that I highly recommend. If you’re reading this, send me a recommendation of a favorite of your own!

I’m also a tiny bit competitive, and love to play Scrabble and Bridge.

What’s one thing you can’t live without?

Live sports. My family and I are serious fans when it comes to American football… go 49ers! You just can’t replicate or replace the energy, action, and pure exhilaration of being in a stadium for a live game. We just watched the 49ers beat the Cowboys at Levi’s Stadium a couple weeks ago!

What’s the best piece of career advice you’ve ever been given?

Get out of your own head and put yourself in other people’s shoes. Even when we disagree about direction, we’re all working on the same team and trying to build the best business we can. Believe in good intentions and work hard to drive the best outcomes. Taking that approach to partnering and problem-solving has helped me become both a better leader and finance professional, and it applies to any role at any level across any business.