Rockstar is hiring an AI-Supercharged Executive Assistant to support U.S.-based healthcare practice owners on a full-time remote basis.
This is a new role at Rockstar.
It's built for an experienced executive assistant who wants to run AI inside a real business, and who knows that the tool is only as good as the person operating it.In this role, you'll own the owner's calendar, inbox, tasks, and daily follow-through, working in a Claude AI environment built specifically for that practice.
Claude drafts.
You review, decide, and send.
The practice owner never touches the technology.
You'll get structured Claude training from your first week, weekly coaching with Rockstar's role lead, and a community of other EAs doing the same work.KEY RESPONSIBILITIESCalendar & SchedulingManage the owner's calendar with consistent color coding, time blocking, and protected focus timeConfirm every meeting's time, attendees, link, and purpose at least 24 hours in advanceUse Claude's calendar connector to prepare daily and weekly calendar summaries, then check them against the real calendar before they go outCoordinate personal appointments and travel where the placement includes itThis is a remote position.Inbox & CommunicationTriage the inbox daily: handle routine items, draft what needs the owner's voice, and escalDraft outbound email through Claude in the practice's brand voice and review every draft before sendingFollow a defined escalation matrix with set response windows for urgent, same-day, and routine itemsAcknowledge email within 4 business hours and flag anything urgent to the owner within 30 minutesTasks, Projects, Meetings & ReportingKeep one task tracker current every day, covering every commitment, owner, and deadlineCoordinate projects across the owner, staff, and vendors,



breaking them into clear steps and tracking milestones through to completionBuild meeting agendas in Claude from what's open on the trackerCreate presentations and slide decks for the owner's meetings, trainings, and partner conversationsTurn meeting notetaker transcripts into same-day recaps with action items assigned to the right peopleDeliver a Daily Summary and Weekly Summary so the owner never has to ask what happenedPull reports from the practice's CRM, EMR, or spreadsheets and spot-check the numbers before they go anywherePractice Coordination & Administrative SupportFollow up with patients and clients after interactions and close the loopSupport referrals, waitlists, and scheduling-related workflowsHandle invoices, PTO tracking, vendor coordination, and compliance remindersWrite and maintain SOPs for recurring workFor practices that include it, monitor social platforms and Google and Yelp reviews, and draft responses for the owner's approvalClaude EnvironmentKeep the practice's brand voice file current as the parch, Shopping, PMax, Demand Gen, YouTube, Merchant Center, GA4, GTM.
Bing is a nice to have.
You are AI native, and you build.
This is a requirement, not a bonus.
You should already be using Claude or equivalent as a working tool rather than a novelty, and you should be able to build and ship a landing page with it.
You can communicate your ideas in English at a native or near native level.
You will be in front of clients constantly.
You need to explain your thinking clearly, sell an idea on its merits, push back when a client is about to force the account into mediocrity, and raise a problem before it becomes a fire.
This matters as much as anything else on this list.
You are skeptical of your own numbers.
You would rather run the holdout than protect the dashboard.
You can work US Eastern business hours for client calls.
Where you live is up to you.
Bonus: you have built or operated your own Shopify store, or you have run Meta at spend too
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📌 Executive Assistant - Remote Work (Juan José Castelli)
🏢 Paired
📍 Juan José Castelli