Upwork Appoints Anthony Kappus as Chief Operating Officer, Elevates Technology and Legal Leaders for Next Chapter of Growth

Executive Leadership Changes - Upwork has appointed Anthony Kappus as its first chief operating officer (COO), effective September 2, 2025, to lead various operational teams [1][2] - Andrew Rabinovich has expanded his role to chief technology officer (CTO), overseeing engineering, IT, and AI initiatives [1][3] - Jacob McQuown has been promoted to chief legal officer (CLO), focusing on legal, compliance, and policy programs [1][4] Strategic Vision and Growth - The leadership team is expected to drive excellence across Upwork's operations, enhancing the company's position in the human and AI-powered work marketplace [2] - Kappus brings over a decade of operational expertise from Redfin, where he led digital revenue and corporate development [2] - Rabinovich's leadership in AI and machine learning is pivotal as Upwork evolves into an AI-native platform, contributing to significant growth [3][4] AI Integration and Economic Impact - Upwork's AI initiatives, particularly the development of Uma™, have led to an increase of over $80 million in gross services volume (GSV) in 2025 [3] - The company has facilitated more than $25 billion in economic opportunity for talent globally, showcasing its impact on the workforce [6]