Upwork CFO Erica Gessert is focusing on ensuring the freelance talent marketplace has “levers in our business that are macro-agnostic” following what she termed as a “breakout quarter,” she told CFO Dive in an interview. The Palo Alto, California-based platform offers an online marketplace for global freelance talent, underpinned by AI, according to its website.

For its second quarter, Upwork reported a 47% year-over-year rise in net income to reach $32.7 million for the quarter ended June 30, as well as recording record revenue of about $195 million — a 1% YoY rise. Adjusted EBIDTA, meanwhile, jumped by 40% YoY to reach $57.1 million, according to its Q2 earnings results released Aug. 7.

Strong growth in AI-related services helped drive these results, a factor that was also enabled by several strategic acquisitions in recent years. The company has made four acquisitions during the past three years. Integrating technologies from those acquisitions into its AI tools drove “some of the great growth that we've been able to show in Q2,” Gessert said.  

As part of its Q2 results, Upwork announced its acquisition of workforce management company Bubty, as well as a plan to acquire Ascen, a “digitally native solution for contingent W-2 workers,” according to its earnings release. The moves follow the acquisitions of Objective AI in 2024 and Headroom, an AI-powered video conferencing platform, in 2023, according to company documents.

However, an important factor of Upwork’s M&A strategy is “we would not have had the flexibility or optionality to do this … without worrying about accessing the capital markets, had we not made this big push to increase profitability [and] cash flow,” Gessert said.

Managing the integration piece

CFOs play a critical role in hitting the right balance between profitability and growth: it’s the job of the finance chief to remind the rest of the business that “profitability gives the business optionality for growth, and that's what it's done for us,” Gessert said. For its Q2, the company reported an 85% jump in free cash flow to reach $65.6 million, according to its earnings report.

Gessert joined Upwork in April 2023 after an eight-year tenure at PayPal, where she served in a number of roles, including a three-year span as its senior vice president, finance and analytics, according to her LinkedIn profile. Her past roles also include a six-year career at telecommunications provider Sprint, where she served in positions including VP, finance operations, postpaid marketing and CFO, Sprint Prepaid.  

Looking ahead, Upwork will continue to make use of its balance sheet to “supplement its growth strategies,” she said, although its unlikely that the company will announce another acquisition during the second half of 2025.

“We are by no means done with M&A,” Gessert said, but “you always need to be conscious of not overdoing it and making sure that your teams can handle the integrations that are happening.”

Creating the space for the integration of tools, processes and talent following the closing of a deal is often the mark of a successful acquisition. At Upwork, Gessert’s team is responsible for everything from the corporate development of the company’s M&A strategy to the integration of such acquisitions throughout the business, she said, an approach she prefers.

In examining such deals, “what you want is a team that is responsible for the end-to-end, so that they really are thinking through the business impacts of that position,” she said.

When integrating various aspects of acquired business, it’s always better to do the “hard work” sooner rather than later, she said, “because, if not, you end up with a bunch of different disparate systems, and it's harder to close your books, and you end up with just a lot of tech debt and pain later on.”

However, in Gessert’s experience the biggest stumbling block to a successful integration is on the cultural side;  “not spending enough time with the new teams” to make sure they feel part of the business, she said.

Data, data everywhere

Upwork is also examining the potential use cases of artificial intelligence, both on its customer-facing platform and inside its own internal processes, Gessert said. AI-related work on the business’ platform saw a 30% rise in gross services volume — the total amount clients spend on such offerings — for its second quarter, speaking to “what's going on out there in the AI world and the acceleration of the work getting done there,” Gessert said.

The number of clients posting AI-related jobs also jumped 38% YoY during the quarter, with the average volume of work from clients engaging in AI tripling, according to the platform’s earnings presentation.

Among other efforts to expand its customer-facing AI services, the company has announced agentic AI services such as its Uma offering , according to company press releases. On Tuesday, Upwork also announced the creation of its “Lifted” platform — a wholly owned AI-powered subsidiary supported by the Bubty and Ascen acquisitions to give “enterprises the technology, talent, and scale to manage their extended workforces efficiently and effectively,” according to the announcement.