Upwork Appoints Anthony Kappus as Chief Operating Officer, Elevates Technology and Legal Leaders for Next Chapter of Growth
Upwork (NASDAQ: UPWK) has announced significant leadership changes to strengthen its executive team. The company appointed Anthony Kappus as its first-ever Chief Operating Officer, effective September 2, bringing his extensive operational expertise from Redfin. Additionally, Andrew Rabinovich has been elevated to Chief Technology Officer, expanding his role to lead engineering and IT alongside AI initiatives.
Under Rabinovich's leadership, Upwork's AI initiatives, including Uma™, have contributed to a $80 million increase in gross services volume (GSV) in 2025. The company also promoted Jacob McQuown to Chief Legal Officer, who has been instrumental in recent acquisitions including Bubty and the pending Ascen deal through Upwork's Enterprise subsidiary.
Upwork (NASDAQ: UPWK) ha annunciato significative modifiche alla leadership per rafforzare il suo team esecutivo. L'azienda ha nominato Anthony Kappus come suo primo Chief Operating Officer, con effetto dal 2 settembre, portando la sua ampia esperienza operativa da Redfin. Inoltre, Andrew Rabinovich è stato promosso a Chief Technology Officer, ampliando il suo ruolo per guidare l'ingegneria e l'IT insieme alle iniziative di intelligenza artificiale.
Sotto la guida di Rabinovich, le iniziative di IA di Upwork, inclusa Uma™, hanno contribuito a un aumento di 80 milioni di dollari nel volume lordo dei servizi (GSV) nel 2025. L'azienda ha inoltre promosso Jacob McQuown a Chief Legal Officer, che è stato determinante nelle recenti acquisizioni, tra cui Bubty, e nell'operazione Ascen in sospeso tramite la controllata Enterprise di Upwork.
Upwork (NASDAQ: UPWK) ha anunciado cambios significativos en su liderazgo para fortalecer su equipo ejecutivo. La compañía nombró a Anthony Kappus como su primer Chief Operating Officer, con efecto desde el 2 de septiembre, aportando su amplia experiencia operativa procedente de Redfin. Además, Andrew Rabinovich ha sido ascendido a Chief Technology Officer, ampliando su papel para dirigir ingeniería y TI junto con las iniciativas de IA.
Bajo el liderazgo de Rabinovich, las iniciativas de IA de Upwork, incluida Uma™, contribuyeron a un aumento de 80 millones de dólares en el volumen bruto de servicios (GSV) en 2025. La compañía también ascendió a Jacob McQuown a Chief Legal Officer, quien ha sido clave en adquisiciones recientes, incluyendo Bubty, y en la operación pendiente con Ascen a través de la filial Enterprise de Upwork.
Upwork (NASDAQ: UPWK)는 경영진을 강화하기 위해 중대한 리더십 변화를 발표했습니다. 회사는 Anthony Kappus를 최초의 최고운영책임자(COO)로 9월 2일부로 임명했으며, 그가 Redfin에서 쌓은 폭넓은 운영 경험을 가져옵니다. 또한 Andrew Rabinovich가 최고기술책임자(CTO)로 승진하여 AI 이니셔티브와 함께 엔지니어링 및 IT를 이끄는 역할을 확대했습니다.
Rabinovich의 지휘 아래 Upwork의 AI 이니셔티브(예: Uma™)는 2025년에 총 서비스 거래액(GSV)을 8천만 달러 증가시키는 데 기여했습니다. 회사는 또한 Jacob McQuown를 최고법무책임자(CLO)로 승진시켰으며, 그는 Bubty를 포함한 최근 인수와 Upwork의 Enterprise 자회사를 통한 진행 중인 Ascen 거래에서 핵심적인 역할을 했습니다.
Upwork (NASDAQ: UPWK) a annoncé d'importants changements au sein de sa direction afin de renforcer son équipe exécutive. La société a nommé Anthony Kappus comme son tout premier Chief Operating Officer, effectif le 2 septembre, apportant sa vaste expertise opérationnelle acquise chez Redfin. De plus, Andrew Rabinovich a été promu Chief Technology Officer, son rôle étant élargi pour diriger l'ingénierie et l'IT aux côtés des initiatives en IA.
Sous la direction de Rabinovich, les initiatives d'IA d'Upwork, dont Uma™, ont contribué en 2025 à une augmentation de 80 millions de dollars du volume brut de services (GSV). La société a également promu Jacob McQuown au poste de Chief Legal Officer, qui a joué un rôle clé dans les acquisitions récentes, notamment Bubty, ainsi que dans l'opération Ascen en attente via la filiale Enterprise d'Upwork.
Upwork (NASDAQ: UPWK) hat bedeutende Führungsänderungen angekündigt, um sein Executive-Team zu stärken. Das Unternehmen ernannte Anthony Kappus zu seinem ersten Chief Operating Officer, mit Wirkung zum 2. September, und bringt damit seine umfangreiche operative Erfahrung von Redfin ein. Zudem wurde Andrew Rabinovich zum Chief Technology Officer befördert, wodurch seine Rolle erweitert wird, Engineering und IT sowie KI-Initiativen zu leiten.
Unter Rabinovichs Leitung haben Upworks KI-Initiativen, einschließlich Uma™, im Jahr 2025 zu einer Steigerung des Bruttodienstleistungsvolumens (GSV) um 80 Millionen US-Dollar beigetragen. Das Unternehmen beförderte außerdem Jacob McQuown zum Chief Legal Officer, der bei den jüngsten Akquisitionen, darunter Bubty, sowie beim laufenden Ascen-Deal über Upworks Enterprise-Tochter eine maßgebliche Rolle gespielt hat.
- AI and customer experience enhancements delivered $80 million lift in gross services volume (GSV)
- Strategic expansion of leadership team with experienced executives from successful companies like Redfin
- Successful integration of AI initiatives through Uma™ platform, positioning Upwork as an AI-native company
- Growth through acquisitions with Bubty deal completed and Ascen acquisition in progress
- Significant organizational restructuring may lead to temporary operational adjustments
- Multiple concurrent leadership changes could create short-term integration challenges
Redfin veteran joins as company’s first COO, Andrew Rabinovich elevated to chief technology officer, and Jacob McQuown becomes chief legal officer, bolstering executive leadership team
PALO ALTO, Calif., Aug. 12, 2025 (GLOBE NEWSWIRE) -- Upwork Inc. (NASDAQ: UPWK), the world’s human and AI-powered work marketplace, today announced that it has appointed Anthony Kappus as the company’s first-ever chief operating officer (COO). Additionally, Andrew Rabinovich has taken on expanded responsibility as chief technology officer (CTO) while continuing to lead AI and machine learning. Jacob McQuown has been promoted to chief legal officer (CLO) to drive Upwork’s leading legal, compliance, and policy program.
“As Upwork continues to lead the industry in the human and AI-powered era of work, our proven leadership team is critical in driving excellence in every area of the business,” said Hayden Brown, president and CEO, Upwork. “Anthony’s deep operational expertise and customer-first mindset, Andrew’s singular AI vision and robust technical knowledge, and Jacob’s measured, strategic approach to every legal matter are tremendous assets for our next chapter of growth.”
Anthony Kappus joins Upwork as COO, effective September 2, to lead a team spanning legal, information security, payments & trust, customer support, and communications. Kappus brings significant operational expertise and marketplace experience from more than a decade spent at Redfin, where he led digital revenue, Redfin’s fastest-growing and most profitable business segment, along with corporate development and legal. He was instrumental in every chapter at the company over that decade, leading a diverse array of functions and teams.
“The breadth of Upwork’s mission and vision was clear from the moment I first met with Hayden and the team,” said Kappus. “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.”
Andrew Rabinovich’s expanded role as CTO, now leading engineering and IT alongside AI and machine learning efforts, reflects Upwork’s evolution into a truly AI-native platform and company, which is enhancing value for customers and catalyzing the company’s growth. Since joining Upwork in late 2023 as part of its acquisition of Headroom, Rabinovich has overseen the development and evolution of Uma™, Upwork’s mindful AI, into an always-on AI work agent, as well as custom domain-specific AI models tuned on Upwork’s proprietary data to deliver better work outcomes for both clients and talent. In 2025, newly-released AI and customer experience enhancements are contributing a more than
“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,” said Rabinovich. “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.”
Finally, Jacob McQuown has been promoted to chief legal officer to lead the legal and policy functions. McQuown has a strong track record over eight years at Upwork, most recently as deputy general counsel leading the announced acquisition of Bubty and agreement to acquire Ascen by Upwork’s new wholly owned Enterprise subsidiary.
About Upwork
Upwork is the world’s human and AI-powered work marketplace that connects businesses with highly skilled, AI-enabled independent talent from across the globe. From Fortune 100 enterprises to entrepreneurs, companies rely on Upwork’s trusted platform and its mindful AI companion, Uma™, to find and hire expert talent, leverage AI-powered work solutions, and drive business transformation. With on-demand access to professionals spanning more than 10,000 skills across AI & machine learning, software development, sales & marketing, customer support, finance & accounting, and more, Upwork enables businesses to scale, innovate, and transform their workforces for the age of AI and beyond.
Upwork’s platform has facilitated more than
Contact:
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