This is the story of eBay’s company-wide Velocity initiative, which doubled engineering productivity across all 5000 engineers, but still could not save the company from its own pathological organizational culture. Once a stock market darling and a pioneering hyperscaler in the 1990s and early 2000s, eBay has been in steady decline since the 2010s. A household name with a flat business, eBay has been unable to make substantive strides in its market reach or its engineering outcomes in the last 15 years. What happened? Randy was a Distinguished Architect at eBay from 2004 to 2011, and returned as Chief Architect and VP of Platform Engineering from 2020 to 2022. As Chief Architect, he led the company-wide Velocity initiative, which doubled engineering productivity across the board. By executing a pretty standard DevOps playbook, this has been an unqualified success on the engineering side. Teams have improved on all of the DORA software delivery metrics, and report better collaboration and developer satisfaction. At the same time, improvements have stagnated, and teams consistently struggle to reach Elite status or to alter the overall trajectory of the business. This talk is an insider’s attempt to make sense of this seeming contradiction between micro-successes and macro-failures, and attempts to abstract 20 years of participation and observation into a set of actionable lessons for any organization attempting to transform itself. We will deep dive into the following: * Strategy and Planning, encompassing Learned Helplessness, the Innovator’s Dilemma, and Centralized Waterfall Planning * Execution and Delivery, covering Massive Coordinated Releases, and the “Feature Factory” * Organizational Culture, epitomizing Westrum’s pathological culture with zero-sum thinking, empire building, risk aversion, and a constitutional inability to acknowledge failures You will learn * how to successfully execute a massive technical transformation across thousands of people using the Accelerate / DevOps playbook * why a technical transformation by itself is not enough * how we would have done things differently in hindsight