Redfin Legal Chief Jumps to Upwork, Building Ties Between Firms

Aug. 13, 2025, 5:26 PM UTC

Upwork Inc. has recruited Redfin Corp.’s longtime top lawyer Anthony Kappus as its first chief operating officer, a role that will see the veteran technology lawyer focused on the company’s rollout of agentic artificial intelligence tools.

Kappus stands to earn more than $10 million from both his departure from Redfin and move to Upwork, a freelance jobs platform and marketplace. Upwork disclosed in a securities filing late Monday that Kappus will receive an annual base salary of $500,000 and about $7.3 million in long-term stock awards for making the move to the Palo Alto, Calif.-based company.

A securities filing ...

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