Rollout playbook

A staged sequence for taking Endpoint AI from your own laptop to the whole organization: pilot, verify, enroll team by team, and measure as you go.

Stage 1: Pilot with a small team

Do not announce anything company-wide yet. Pick one team that already leans on AI, complete the Get started wizard yourself, then send that team enrollment invites from People. Each person opens the invite link and connects Harriet Desktop (or Claude Desktop, where your organization uses it).

Before expanding beyond the pilot, confirm identity works: SSO or account linking should behave as expected for every pilot user, and roles should match who may configure integrations and skills versus who only consumes them.

Keep the pilot running long enough to see a full business rhythm. If a skill touches payroll or HRIS data, that means at least one complete pay cycle before you call it proven.

Stage 2: Verify integrations and skills

Run this checklist before you turn on any new connector or skill for a wider audience:

• Review queue ownership. Confirm who may submit, approve, or request changes for connectors and package skills. The submitter and reviewer should not be the same person unless your policy allows it. See the review queue.
• Data and compliance. Confirm data residency and DPA coverage for each vendor you connect, and grant least-privilege OAuth scopes or API keys, removing unused access.
• Tool behavior. After syncing tools on a new MCP connector, verify tool permissions and sandbox behavior match your risk appetite.
• Operational readiness. Write down who rotates credentials after go-live and who watches for failed syncs, rate limits, or expired auth.
• Read before write. Do not enable write skills in production until the read paths are stable.

Stage 3: Enroll team by team

Expand one team at a time rather than opening the gates. For each team:

1. Build the team's profile. Bundle the skills, connectors, and settings that team needs into a profile and assign it to the team. Every enrolled device on the team then receives the same configuration.
2. Send enrollment invites. Add people in Manage users first, then send invites from People. Each invite is a secret link the person opens to connect a device.
3. Or push through MDM. For fleets you already manage, enroll devices via MDM instead of individual invites.
4. Confirm the first sync. Open the team in Teams and check members show linked devices and successful calls before moving to the next team.

Communicating with employees

A short employee-facing note per wave beats one big announcement. Say what changed, what they can now ask their AI to do, and what to do when something fails. Set expectations early: Harriet works from your company's skills and connected systems, not a general open-ended promise. Always give a fallback path, such as a ticket or an email alias, for sensitive or novel requests.

Train one or two champions per team on how to phrase requests and when to escalate. Champions absorb most early questions and surface the real gaps.

Measuring adoption

The Dashboard gives you the rollout scoreboard. The Adoption overview panel tracks three coverage bars: Users with device linked, Users with any assignment, and Teams with profile assigned. The Tool call activity chart shows MCP proxy successes and errors by day, so a wave that enrolled but never calls tools is visible within a week.

For cost and usage per team, open LLM Usage, or check the per-team usage panel on each team's detail page. See usage analytics and budgets.