Short answer: Start with shared rules and a small pilot, not licenses for everyone. Then measure usage and cost.
These are my lessons from leading the Cursor rollout at Elementor, in an engineering organization of 50+ engineers.
1. Pilot before rollout. A small group of volunteers, four to six weeks, and real tasks.
2. Shared rules files. Repo-level Cursor rules fix code style, conventions and common mistakes. Without them every developer gets different results.
3. An internal community. A forum or "guild" where developers share prompts, tricks and failures. Peer learning is faster than top-down training.
4. Code review. Code written by AI must go through human review. You can add an automated review that learns from the team's comments and stays updated with the rules.
5. Measure usage and cost. Without measurement, the costs surprise you. Track usage per developer, and check whether it translates into output.
6. Security and privacy. Define which repositories and secrets are not exposed to the tool.
Common mistake: assuming the tool alone will improve productivity. The process around it is what matters.
I accompany teams through this kind of rollout: diagnosis, rules, automated code review and measurement. Details: https://israeli-ai-agency.pages.dev/services/ai-native/. To get in touch: LinkedIn https://il.linkedin.com/in/ofershap or email ofers@mail.instinct.com (a business WhatsApp line will be added soon)