Upwork names Anthony Kappus as first COO, promotes two executives

Upwork Inc. (NASDAQ: UPWK) appointed Anthony Kappus as its first chief operating officer and promoted two internal executives to expanded leadership roles, according to a company statement.

Kappus, who spent more than a decade at Redfin where he led digital revenue operations, will begin his role September 2. He will oversee legal, information security, payments, customer support, and communications functions.

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

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

According to the company, AI and customer experience enhancements released in 2025 are contributing more than $80 million in gross services volume. Rabinovich has overseen development of Uma, Upwork's AI platform, and custom AI models using the company's proprietary data.

Upwork operates a marketplace connecting businesses with independent talent across more than 10,000 skills. The platform has facilitated more than $25 billion in economic activity, according to the company statement.

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