PagerDuty's pricing trajectory is following the exact same playbook as Datadog. Start cheap enough that teams adopt it without finance approval, then jack up per-seat pricing once it's embedded in every runbook and escalation policy.

The insidious part with on-call tooling specifically is that switching costs are higher than almost any other category. Your escalation chains, schedules, integrations with monitoring, incident templates, post-mortem workflows - it all becomes organizational muscle memory. Migrating monitoring backends is a weekend project compared to migrating on-call routing.

What I've seen work: teams that treat on-call routing as a thin layer rather than a platform. If your schedules live in something portable (even a YAML file synced to whatever tool) and your alert routing is OpenTelemetry-native, swapping the actual dispatch tool becomes manageable. The teams that get locked in are the ones who build their entire incident process inside PD's UI.