Upwork CFO Erica Gessert said the company is focused on ensuring the freelance talent marketplace has "macro-insensitive business levers," after she called the second quarter a "breakout quarter." The Palo Alto, California-based platform, according to its website, offers an online marketplace for global freelance talent, powered by artificial intelligence.

In the second quarter ended June 30, Upwork's net income rose 47% year-over-year to $32.7 million, whilesetting a record revenue of approximately $195 million, up 1% year-over-year. Adjusted EBITDA rose 40% year-over-year to $57.1 million, according to the second-quarter earnings report released on August 7.

Strong growth in AI-related services drove these results, a factor also supported by several strategic acquisitions in recent years. The company completed four acquisitions over the past three years. Gessert said integrating the technologies from these acquisitions into its AI tools drove "some of the significant growth we demonstrated in the second quarter."

As part of its second-quarter results, Upwork announced the acquisition of workforce management company Bubty and plans to acquire Ascen—a "digitally native solution for contingent W-2 workers" company, according to its earnings release. Previously, the company acquired Objective AI in 2024 and AI-driven video conferencing platform Headroom in 2023, according to company filings.

However, Gessert noted a key factor in Upwork's M&A strategy: "If we hadn't pushed hard on improving profitability and cash flow, we wouldn't have had the flexibility or the choice to make these moves without worrying about access to capital markets."

Managing the integration piece

The CFO plays a key role in balancing profitability and growth: the finance chief's job is to remind business teams that "profitability provides optionality for growth, and that's what it's done for us," Gessert said. In the second quarter, the company's free cash flow rose 85% year-over-year to $65.6 million, according to its earnings report.

Gessert joined Upwork in April 2023, after spending eight years at PayPal in various roles, including three years as senior vice president and head of finance and analytics, according to her LinkedIn profile. She previously spent six years at telecommunications carrier Sprint, holding positions such as vice president of financial operations, postpaid marketing, and CFO of Sprint Prepaid.

Going forward, Upwork will continue to use its balance sheet to "supplement growth strategies," she said, but the company is unlikely to announce another acquisition in the second half of 2025.

"We are far from done with M&A," Gessert said, but "you always need to be careful not to overdo it, ensuring your team can handle the integrations that are underway."

Creating space for integrating tools, processes, and talent after a deal closes is often a hallmark of successful acquisitions. At Upwork, Gessert's team is responsible for everything from the corporate development of the company's M&A strategy to how such acquisitions are integrated across the business, which she said is her preferred approach.

When reviewing such deals, "you want a team that owns it end-to-end, so they can really think about the business impact of that role," she said.

When integrating various aspects of an acquired business, it's best to do the "hard work" as early as possible, she said, "because if you don't, you end up with a bunch of different disparate systems, harder to close the books, and you just accumulate a lot of technical debt and pain down the road."

However, in Gessert's experience, the biggest obstacle to successful integration lies on the cultural side; "not spending enough time with the new team" to ensure they feel part of the business, she said.

Data everywhere

Upwork is also exploring potential use cases for artificial intelligence, both in customer-facing platforms and internal processes, Gessert said. In the second quarter, gross services volume for AI-related work on the platform—total customer spending on such services—grew 30%, reflecting "what's happening in the AI world and the acceleration of work there," Gessert said.

During the quarter, the number of customers posting AI-related jobs rose 38% year-over-year, and the average workload of customers engaging with AI tripled, according to the platform's earnings presentation.

In other efforts to expand customer-facing AI services, the company has announced the launch of agentic AI services, such as its Uma product, according to a company press release. On Tuesday, Upwork also announced the creation of its "Lifted" platform—a wholly owned AI-driven subsidiary, supported by the Bubty and Ascen acquisitions, designed to "provide businesses with the technology, talent, and scale to efficiently and effectively manage their extended workforce," according to the announcement.