Upwork names first COO, reshapes global leadership team
CALIFORNIA, UNITED STATES — Upwork, a global work marketplace, has announced the appointment of Anthony Kappus as its first-ever Chief Operating Officer (COO).
The move is part of a broader executive shake-up that includes Andrew Rabinovich’s elevation to Chief Technology Officer (CTO) and Jacob McQuown’s promotion to Chief Legal Officer (CLO), reflecting the company’s commitment to rapid innovation and industry leadership in human and AI-powered work.
Anthony Kappus joins Upwork as Chief Operating Officer
Effective September 2, Kappus will oversee a cross-functional team spanning legal, information security, payments and trust, customer support, and communications.
Kappus joins Upwork with over a decade of operational experience at Redfin, where he drove digital revenue and corporate development.
“Upwork is at the vanguard of how AI is transforming knowledge work. I’m thrilled to help scale Upwork’s global marketplace to both an expanding range of clients, from large enterprises to small businesses, and talented professionals around the world,” Kappus remarked.
Upwork boosts AI, legal leadership with CTO, CLO appointments
Rabinovich, previously head of AI and machine learning, now broadens his purview as CTO to include engineering and IT. Rabinovich’s vision has steered the development of Upwork’s AI agent, Uma, delivering custom domain-specific AI models that have driven significant business growth—including an $80 million lift in gross services volume (GSV) in 2025.
“Today, thanks to our top-tier AI and engineering team’s rapid innovation, AI is at the core of nearly everything new that Upwork builds for our customers,” he said.
“Upwork has become an AI company, but we’re still in the early days of our roadmap for human-centered AI, and we have so much more to deliver in the coming quarters and years.”
Meanwhile, McQuown takes over as CLO after eight years at Upwork and multiple high-profile acquisitions.
According to CEO Hayden Brown, “Anthony’s deep operational expertise and customer-first mindset, Andrew’s singular AI vision, and Jacob’s strategic approach are tremendous assets for our next chapter of growth.”
Upwork expands beyond freelance marketplace
Founded in Palo Alto, Upwork operates across the Americas, Europe, Asia, Africa, and Australia, servicing clients and freelancers in over 180 countries. The platform connects businesses—from Fortune 100 firms to startups—with skilled, independent talent in more than 10,000 fields, including AI, software engineering, sales, finance, and support services.
Upwork’s platform, powered by its AI assistant Uma, has facilitated more than $25 billion in economic opportunity globally, helping companies scale and transform their workforces for the AI era.
Upwork recently moved beyond its core freelance marketplace with two acquisitions aimed at capturing a larger share of the corporate staffing market. The company has acquired Bubty, a freelancer management system (FMS) and staffing platform, and also signed a definitive agreement to acquire Ascen, a global compliance and employer-of-record (EOR) provider.
