Upwork Announces New COO, CTO, and CLO Appointments

Upwork Inc. has appointed Anthony Kappus as its first-ever chief operating officer (COO), effective September 2. Andrew Rabinovich has taken on expanded responsibility as chief technology officer (CTO) while Jacob McQuown has been promoted to chief legal officer (CLO) to drive Upwork's leading legal, compliance, and policy program. Kappus joins from Redfin, where he led digital revenue and corporate development. Rabinovich oversees engineering, IT, AI, and machine learning efforts, while McQuown has a strong track record at Upwork, most recently leading the acquisition of Bubty and Ascen.

Upwork Inc. (NASDAQ: UPWK) has made significant executive appointments to bolster its leadership team. Anthony Kappus has been appointed as the company's first-ever Chief Operating Officer (COO), effective September 2. Additionally, 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, COO
Kappus, who joins from Redfin, brings over a decade of operational expertise and marketplace experience. He led digital revenue and corporate development at Redfin, instrumental in the company's growth. At Upwork, Kappus will oversee legal, information security, payments & trust, customer support, and communications [1].

Andrew Rabinovich, CTO
Rabinovich, who has been with Upwork since late 2023, will now lead engineering and IT alongside AI and machine learning efforts. His expanded role reflects Upwork's evolution into an AI-native platform. Rabinovich has overseen the development of Uma™, Upwork's mindful AI, and custom domain-specific AI models, contributing to a $80 million lift in gross services volume (GSV) in 2025 [2].

Jacob McQuown, CLO
McQuown, with a strong track record at Upwork, will lead the legal and policy functions. Most recently, he led the acquisition of Bubty and the agreement to acquire Ascen by Upwork's new wholly owned Enterprise subsidiary [3].

These appointments come at a time when Upwork is experiencing growth, as seen in its Q2 2025 earnings where revenue exceeded estimates. The company expects Q3 revenue to range between $190.0M - $195.0M and adjusted EPS to be between $0.28 - $0.30 [2].

References:
[1] https://finance.yahoo.com/news/upwork-appoints-anthony-kappus-chief-130000316.html
[2] https://www.marketscreener.com/news/upwork-inc-announces-executive-appointments-ce7c51dadb80f62c
[3] https://www.marketscreener.com/news/upwork-inc-announces-executive-appointments-ce7c51dadb80f62c