Kama'āina AI / Cowork Setup
Claude Cowork · set up for businessEveryone's tried the chatbot. Almost nobody has it set up around their real work. I configure Cowork for your team — your projects, your files, your tools — and build the skills that turn it from a novelty into staff.
Most business owners have a Claude subscription and treat it like a smarter search box. Meanwhile it can read your files, use your tools, remember how your business works, and run the same job the same way every week.
The difference isn't the AI. It's whether someone sat down and built it around what you actually do.
A skill is a saved way of doing one recurring job. Build it once, and every time that job comes up it gets done the same way — by you, or by anyone on your staff. Here's a real starter set from a Maui clinic:
Learns how you actually write from a month of your own emails, then every draft sounds like your business instead of like a robot.
Welcomes, post-visit follow-ups, re-activation for people who drifted. Drafted in seconds, in your voice, ready for you to send.
Appointment confirmations and reminders written for your schedule and your tone, not a template from your booking software.
Timed to go out after a good visit, phrased so people actually write one. The single cheapest thing you can do for local search.
Turns a new client's forms into a short brief you can read in thirty seconds before you walk into the room.
The report you rebuild every Monday. The proposal you rewrite from scratch. Tell me on the call and it goes in the build.
Yours to keep. The skills I build for you live in your workspace, in your account. If we never speak again you keep every one of them, and they keep working.
A couple of hours with you and whoever else touches the day-to-day. We list what actually repeats — not what the org chart says, what the week actually looks like.
Workspace, projects, and skills built around that list. Connectors wired into the tools you already pay for, with access scoped before anything gets connected.
A live session with your staff on their own real work, not a demo. Plus written docs for whoever you hire next.
I come back after you've lived with it. What's getting used, what isn't, what needs fixing. Included, not extra.
For businesses that keep finding new work to hand over. New skills as they come up, tuning as you grow, onboarding for new staff, and someone to text when something breaks. Month to month, cancel anytime — and plenty of clients never take it.
You buy seats directly from Anthropic — roughly $20/seat/month on the Team plan, billed annually. I don't resell it and I don't mark it up. You own the account; I just set up what's inside it.
You have staff, recurring paperwork, and a subscription you're barely using. You keep rebuilding the same document. You've hired someone and had to re-explain everything from scratch. You're the bottleneck on work that doesn't need you.
You're a one-person shop with no repeating admin, or you genuinely enjoy tinkering with this stuff yourself — in which case save the money and go build it. I'd rather tell you that on the call than take the fee.
Cowork runs on any paid Claude plan — Pro, Max, Team, or Enterprise. For a business with staff you want Team (about $20/seat/month billed annually), because it gives you shared admin controls and lets me curate which tools your people can reach. If it's just you, Pro is fine. You buy the seats directly from Anthropic; I don't resell them and I don't mark them up.
Technically yes, and some people should. The setup isn't the hard part — deciding what to build is. Most owners open it, ask it a few questions, get a decent answer, and never come back, because nothing was built around their actual recurring work. That gap is what the $1,500 buys.
It depends entirely on how it's configured, which is most of why this is a service and not a download. We scope what Claude can reach before connecting anything. Regulated records — patient files especially — stay out of systems that shouldn't hold them, and admin controls let you approve write access per tool rather than handing over blanket permission.
That's the real failure mode, not the technology. It's why training is in the base price instead of an add-on. If your staff can't name three things it does for them by the end of the session, the setup was wrong and I'd rather fix it then than find out in a month.
About two weeks. A few hours of my time with you up front to map the work, a week of building, then the training session. You're running before the month is out.
No — and I mean that. The setup stands on its own and you own everything I build. The retainer is for businesses that keep finding new work to hand over. Plenty of clients do the setup, run it for a year, and call me when something changes.
Free 15-minute call. Tell me what eats your time, and I'll tell you exactly what I'd build to take it off your plate. No deck, no pressure.
Jesse Kuhio Kalani Best
Founder · Kama'āina AI Co. · Maui, Hawai'i