Owen Jennings

Before joining Block, Jennings worked on the investment team at Bridgewater Associates. He then spent more than a decade at Block, formerly Square, where he led business operations for Square and later served as chief operating officer of Cash App.⁠[1][2]

On September 9, 2024, Block COO and CFO Amrita Ahuja announced leadership changes at the Goldman SachsGoldman SachsGoldman Sachs is an American financial services group headquartered in New York whose businesses include investment banking, securities trading, asset management, and wealth management. It traces its origins to the commercial paper business Marcus Goldman founded in 1869; it listed on the New York Stock Exchange in 1999 under the ticker GS and became a bank holding company in 2008. David Solomon serves as chairman and chief executive officer.Open the full entry Communacopia + Technology conference: Jennings moved from Cash App COO to overseeing Block’s business functions across product, marketing and customer success a role he had begun that August. Block’s leadership profile describes him as Business Lead overseeing the company’s product, operations and customer support functions, and lists him among its executive officers.⁠[3][1]

In December 2024 Jennings took part in a fireside chat with UBSUBSUBS is a global financial group headquartered in Zurich, Switzerland, operating wealth management, Swiss personal and corporate banking, asset management and investment banking. Its modern bank emerged from a 1998 merger, its holding company was incorporated in 2014, and it acquired Credit Suisse in 2023.Open the full entry analyst Tim Chiodo at the 2024 UBS Technology and AI Conference, discussing Square’s Orders platform, Cash App’s shift from a peer-to-peer payments app to broader financial services, and the more than $22 billion in loans underwritten through Square Loans since its launch. He said, “Our purpose as a company is economic empowerment — we see expanding access to capital as a critical part of that work.”⁠[4]

On April 1, 2026, a16zAndreessen HorowitzAndreessen Horowitz (a16z) is a venture capital firm founded in 2009 by Marc Andreessen and Ben Horowitz. It invests from the seed stage through the growth stage and provides operational support to its portfolio companies.Open the full entry released the episode “What Happens When a Public Company Goes All In on AI,” titled on YouTubeYouTubeYouTube is Google’s video-sharing and creator platform, founded in 2005 by Steve Chen, Chad Hurley, and Jawed Karim and acquired by Google in 2006. Built around video uploading, viewing, and creator earnings, the platform has developed Shorts, YouTube Music, Premium, YouTube TV, and products for children, and is headquartered in San Bruno, California, United States.Open the full entry “How to Reorg After AI Changes Everything | Block's Owen Jennings on the a16z Show.” Andreessen Horowitz general partner David HaberDavid HaberDavid Haber is an investor and entrepreneur and a New York-based general partner at Andreessen Horowitz (a16z). He previously invested at Spark Capital, co-founded small-business lender Bond Street and worked in Goldman Sachs strategy after its acquisition of the company.Open the full entry spoke with Jennings about how Block rebuilt itself around AI agents, small squads and internal tools such as Goose and Builder Bot after restructuring more than 40% of its workforce, how teams of three now do what teams of 14 used to, and how Block is shipping AI-native products such as Money Bot and Manager Bot that generate custom interfaces on the fly for tens of millions of users; the conversation also covered the shape of the Square, Cash App and Afterpay businesses.⁠[5][6]