Upwork names Anthony Kappus as first chief operating officer

PALO ALTO - Upwork Inc. (NASDAQ:UPWK), a company currently maintaining strong financial health according to InvestingPro metrics, announced Tuesday the appointment of Anthony Kappus as the company’s first-ever chief operating officer, effective September 2, as part of several executive leadership changes.

Kappus, who spent over a decade at Redfin where he led digital revenue and corporate development, will oversee legal, information security, payments, customer support, and communications teams at the work marketplace.

The company also elevated Andrew Rabinovich to chief technology officer, expanding his responsibilities to include engineering and IT alongside his current oversight of AI and machine learning. Rabinovich joined Upwork in late 2023 through the acquisition of Headroom.

Additionally, Jacob McQuown has been promoted to chief legal officer after eight years with the company, most recently serving as deputy general counsel.

"As Upwork continues to lead the industry in the human and AI-powered era of work, our proven leadership team is critical in driving excellence in every area of the business," said Hayden Brown, president and CEO of Upwork, in the press release.

According to the company, AI and customer experience enhancements released in 2025 are contributing more than $80 million in gross services volume. With impressive gross margins of 77.9% and trading at an attractive P/E ratio of 7.3, Upwork describes itself as a marketplace connecting businesses with independent talent across various skills including AI, software development, marketing, and finance. InvestingPro analysis suggests the stock is currently undervalued, with multiple analysts revising earnings estimates upward.

The work marketplace has facilitated over $25 billion in economic opportunity for talent globally, according to the company statement. With last twelve months revenue of $772.9 million and strong liquidity metrics, Upwork continues to demonstrate solid financial performance. For detailed insights and additional financial metrics, check out the comprehensive Pro Research Report available on InvestingPro.

In other recent news, Upwork Inc. reported stronger-than-expected second-quarter 2025 earnings. The company posted earnings per share of $0.35, surpassing analyst expectations of $0.27, marking a 29.63% surprise. Revenue for the quarter reached a record $194.9 million, exceeding the anticipated $187.56 million. These results were bolstered by Upwork’s AI features, which enhanced client activity and spending per active client, despite challenging macroeconomic conditions. Additionally, Goldman Sachs adjusted its price target for Upwork from $25.00 to $24.00 while maintaining a Buy rating. This adjustment came after evaluating the company’s earnings report, which exceeded guidance ranges for revenue, adjusted EBITDA, and adjusted EPS. The robust performance highlights Upwork’s resilience and adaptability in the current economic climate.

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