Upwork Names New COO and Expands Roles for CTO and CLO

Upwork has appointed Anthony Kappus as its first-ever chief operating officer, while Andrew Rabinovich has taken on expanded responsibility as chief technology officer, and Jacob McQuown has been promoted to chief legal officer. These appointments aim to drive the company's growth and strengthen its leadership team.

PALO ALTO, Calif., Aug. 12, 2025 — Upwork Inc. (NASDAQ: UPWK), the global human and AI-powered work marketplace, has announced significant executive appointments aimed at driving growth and strengthening its leadership team. Anthony Kappus has been appointed as the company's first-ever chief operating officer (COO), while Andrew Rabinovich has taken on expanded responsibilities as chief technology officer (CTO), and Jacob McQuown has been promoted to chief legal officer (CLO).

Anthony Kappus joins Upwork as COO, effective September 2, to lead teams spanning legal, information security, payments & trust, customer support, and communications. With over a decade of operational expertise and marketplace experience at Redfin, Kappus will bring a customer-first mindset to scale Upwork’s global marketplace for both enterprises and talented professionals worldwide [1].

Andrew Rabinovich's expanded role as CTO reflects Upwork’s evolution into a truly AI-native platform. Since joining Upwork in late 2023, Rabinovich has overseen the development of Uma™, Upwork’s mindful AI, into an always-on AI work agent. This has led to significant enhancements in AI and customer experience, contributing a more than $80 million lift in gross services volume (GSV) for the company in 2025 [1].

Jacob McQuown, with a strong track record at Upwork, has been promoted to CLO to lead the legal and policy functions. His recent role as deputy general counsel involved leading the announced acquisition of Bubty and the agreement to acquire Ascen by Upwork's new wholly owned Enterprise subsidiary [1].

These appointments signal Upwork's commitment to leveraging AI and technology to enhance its platform and drive business transformation. The new leadership team is well-positioned to navigate the evolving landscape of the AI-powered work marketplace and capitalize on opportunities for growth.

References:
[1] https://www.globenewswire.com/news-release/2025/08/12/3131777/0/en/Upwork-Appoints-Anthony-Kappus-as-Chief-Operating-Officer-Elevates-Technology-and-Legal-Leaders-for-Next-Chapter-of-Growth.html
[2] https://www.marketscreener.com/news/upwork-inc-announces-executive-appointments-ce7c51dadb80f62c