How Engineering Leaders Use Feature Flags to De-Risk Replatforming and Speed Up Migration

Cloud migrations, API rewrites, and architecture transformations rarely fail because engineers built the wrong system — they fail because leaders rely on “big bang” releases that tie deployment and release into a single moment of maximum risk. According to industry research, more than half of large-scale transformations fail to achieve their intended benefits within three years.

This community roundtable will explore how modern engineering leaders are using feature flags and experimentation to deliver migrations safely, incrementally, and measurably. You’ll learn how progressive rollout, safe production testing, and outcome-driven metrics turn replatforming from a fragile one-shot cutover into a reversible, data-guided evolution.

We’ll cover:

1. How to replace big-bang releases with controlled, observable progressive rollouts
2. How to measure “Is it better?” instead of “Did it deploy?” across performance, cost, and stability
3. How governance, auditability, and CI/CD integration enable safe autonomy at scale
4. Real examples of how teams used flags to modernize pipelines, retire legacy systems, and validate new cloud components without disruption

Whether you’re migrating monoliths, replacing APIs, rebuilding frontends, or moving to cloud infrastructure, this session will give you a proven roadmap for reducing risk while accelerating delivery.

We look forward to seeing you there!

Questions? Contact [email protected]