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?

I was a Distinguished Architect at eBay from 2004 to 2011, and returned as VP of Platform Engineering and Chief Architect from 2020 to 2022. As Chief Architect, I led the company-wide Velocity initiative, which has continued to double engineering productivity across the board. By executing the DevOps playbook, this has been an unqualified success. In the two years I was there, and continuing over the three years since, 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:

• Technology Evolution, moving over time Innovator to Laggard, from early adopter to isolated holdout
• Business Strategy, encompassing Learned Helplessness, the Innovator’s Dilemma, and Centralized Planning
• Organizational Culture, epitomizing Westrum’s pathological culture with zero-sum thinking, empire building, risk aversion, and a constitutional inability to acknowledge failures

Come for the Continuous Delivery story; stay for the unvarnished retrospective on eBay’s hidebound engineering and organizational culture. As the old joke goes, “I may be slow, but I do poor work!”