Descriptions:
The Pragmatic Engineer podcast sits down with Robert Erez, a CI/CD veteran with over a decade in the field and one of the early engineers at Octopus Deploy, for a deep exploration of modern deployment practices and how AI is beginning to reshape them.
The conversation covers the full arc of CI/CD evolution: from manual weekly release windows and change advisory boards (as Erez and host Gergely Orosz both experienced on the Skype for Web team in the mid-2010s) through canary deployments, blue-green releases, and feature toggles. Erez makes the case for prioritizing “roll forward” over rollback strategies, noting that most teams who claim to roll back regularly have simply never encountered a schema migration mid-rollout — a scenario that exposes rollback as far more complex than assumed.
The episode also addresses GitOps, platform teams, and the organizational shift from siloed DevOps groups back toward developer ownership of deployment pipelines at scale. Crucially, a dedicated segment asks what AI is changing in CI/CD: as AI-assisted coding dramatically increases the volume of code being written and shipped, the pressure on deployment infrastructure to handle higher change frequency safely becomes a central engineering challenge. The episode draws on Erez’s experience watching these patterns play out across Octopus Deploy’s customer base, including unconventional deployments like Kubernetes clusters running on oceangoing research vessels.
📺 Source: The Pragmatic Engineer · Published June 17, 2026
🏷️ Format: Podcast
