Upwork appoints Anthony Kappus as first COO effective Sept 2; promotes Rabinovich to CTO, McQuown to CLO

UPWORK, INC

Anthony Kappus named COO, effective Sep 2, 2025; previously Redfin Chief of Digital Revenue and Chief Legal Officer.
Kappus receives $500K base salary, 60% target bonus, $7.25M RSU award vesting over 4 years.
Andrew Rabinovich expanded to CTO, leading engineering, IT, and AI/ML; Jacob McQuown promoted to CLO.
AI enhancements contributed >$80M lift in GSV in 2025, per the press release.

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