Pomeroy Mac AI Assistant Onboarding (5-7 days)
A fixed-scope engagement that installs Pomeroy on a client's Mac, wires their AI assistant to Mail, Calendar, and Contacts, and hands over documented prompt workflows the client can run without an agency on retainer. Time: 5-7 days.
By InnovaAI ResearchPublished
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Pomeroy Mac AI Assistant Onboarding (5-7 days)
A fixed-scope engagement that installs Pomeroy on a client's Mac, wires their AI assistant to Mail, Calendar, and Contacts, and hands over documented prompt workflows the client can run without an agency on retainer.
- Client machine runs macOS and the assistant they want to use appears on Pomeroy's supported list (Claude Desktop, Cursor, VS Code, Cline, or one of the 17+ others)
- Named client-side owner who can approve macOS permission prompts for Mail, Calendar, and Contacts during the install window
- Agency technician has a Mac available for a dry run of the Pomeroy menu-bar install and one-click assistant connection before touching client hardware
- Written scope naming which native apps are in bounds, since Pomeroy connects 9 apps and each added app widens the permission surface
- Client accepts that Pomeroy is a local, single-Mac tool with no multi-tenant console, so the engagement is scoped per machine
- 1.Inventory the client's Mac apps and confirm which of Pomeroy's 9 connected apps they actually need
- 2.Check the client's preferred assistant against Pomeroy's integration list and flag any that require the local HTTP endpoint instead of native MCP
- 3.Agree the permission boundary in writing: Mail read, Calendar read, Contacts read, and nothing outside that set
- 1.Install the Pomeroy menu-bar app on the client Mac and confirm the menu-bar icon is live
- 2.Run the one-click connection for the client's primary assistant and verify it registers in Pomeroy
- 3.Generate the configuration snippet for any secondary assistant that does not support one-click setup
- 1.Grant macOS permissions for Mail and Calendar through Pomeroy's central permission panel
- 2.Test that the assistant can read a calendar event and a mail thread through the local MCP server
- 3.Add Contacts permission only if the client's workflow needs it, then re-test
- 1.Build prompt workflow one: draft replies to inbound mail using Calendar context for scheduling
- 2.Build prompt workflow two: summarize the week's calendar and surface conflicts before they land
- 3.Save both workflows as written runbooks with the exact prompt text the client will paste
- 1.Walk the client owner through the Pomeroy menu bar, permission toggles, and how to revoke access per app
- 2.Show them where the weekly action allowance is consumed and what happens when it runs out
- 3.Hand over the runbook and record a short screen capture of each workflow running end to end
- 1.Run a supervised session where the client drives both workflows while the agency watches
- 2.Log every failure mode observed and patch the prompt text where the assistant misread Mail or Calendar data
- 3.Confirm the client can add or remove an assistant connection without agency help
- 1.Deliver the final runbook, permission map, and assistant inventory as a single handover pack
- 2.Recommend the Pomeroy One-time licence at $19 if the client's usage will exceed the Free tier's 50 actions every week
- 3.Close with an optional quarterly review slot priced separately, since Pomeroy itself carries no subscription to resell
The tool cost is effectively zero to $19 one-time, so the $1,150 fee is almost entirely agency labour at roughly $115 per hour across a 10-hour build. Margin holds because the client is paying for permission scoping, prompt runbooks, and supervised handover, none of which Pomeroy provides on its own. The ceiling is real: Pomeroy has no multi-tenant console or white-label layer, so each new Mac is a fresh build rather than a resold seat.
- Pomeroy permission map showing which of the 9 connected apps are enabled and which macOS permissions each assistant holds
- Assistant inventory listing every connected assistant (Claude Desktop, Cursor, VS Code, Cline, or others) with its connection method, one-click or generated snippet
- Two documented prompt workflows with exact prompt text for Mail drafting and Calendar conflict review
- Screen-capture walkthrough of the Pomeroy menu bar, permission toggles, and per-app revocation steps
- Licence recommendation memo stating whether the client stays on Free or buys the $19 One-time licence, with the 50-actions-per-week threshold as the trigger
The client's named owner can independently connect a new assistant through Pomeroy, run both documented workflows against live Mail and Calendar data, and revoke any app permission from the menu bar without contacting the agency.
More on Pomeroy
- StrategyWhy Pomeroy's $19 One-Time Price Changes Agency Mac Support Economics
- ConceptPomeroy Permission Perimeter
- Evaluation RuleWhen to Adopt Pomeroy: Mac-Only Teams Serving 1-3 Local Clients
- Decision FrameworkPomeroy: Buy vs Skip (Mac-Only AI Assistant Workflows)
- Failure PatternThe Pomeroy Shared Allowance Trap: Why Agencies Fail With Pomeroy on Multi-Mac Delivery
- Operating ProcedurePomeroy Client Mac Onboarding (Onboarding)