Upwork (NASDAQ: UPWK) is reorganizing its leadership bench to match its ambitions in the AI-powered work marketplace. The company has named Anthony Kappus its first chief operating officer, expanded CTO Andrew Rabinovich’s mandate, and promoted Jacob McQuown to chief legal officer.
CEO Hayden Brown framed the moves as a way to fuel “the next chapter of growth” in what she calls the “human and AI-powered era of work.”
A Marketplace Veteran Steps In
Kappus, who joins on September 2, will oversee a portfolio spanning legal, security, payments, trust, customer support, and communications. His decade at Redfin saw him lead its fastest-growing, most profitable segment—digital revenue—while touching everything from corporate development to legal ops. That blend of operational and marketplace experience will be key as Upwork scales to serve both Fortune 500 clients and solo freelancers.
“The breadth of Upwork’s mission and vision was clear from the moment I met the team,” Kappus said, calling the platform “at the vanguard” of AI’s impact on knowledge work.
CTO Role Grows Alongside AI Footprint
Rabinovich, who joined via Upwork’s 2023 acquisition of Headroom, now takes on engineering and IT in addition to AI and machine learning. His team’s crown jewel, Uma™—Upwork’s “mindful AI” work agent—has evolved into an always-on assistant that pairs proprietary data with domain-specific AI models.
That AI push isn’t just a branding exercise: 2025’s AI and customer experience upgrades have already contributed over $80 million in gross services volume (GSV).
“Upwork has become an AI company,” Rabinovich said. “We’re still in the early days of our roadmap for human-centered AI.”
Legal Leadership for a Growth-By-Acquisition Play
McQuown, now CLO after eight years with the company, has been central to recent expansion moves, including the acquisition of Bubty and the pending purchase of Ascen. He now heads the legal, compliance, and policy apparatus as Upwork balances innovation with regulatory guardrails.
The Big Picture
Upwork’s leadership shuffle comes as the talent platform space becomes increasingly AI-driven, with rivals like Fiverr also investing heavily in AI-powered matching and productivity tools. By marrying operational depth with a tech-first growth strategy, Upwork is betting that its blend of human expertise and proprietary AI will define the next phase of the global freelance economy.
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