AI-Powered Executive Assistant for Healthcare Leaders Remote

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 RESPONSIBILITIES

Calendar & Scheduling

• Manage the owner's calendar with consistent color coding, time blocking, and protected focus time
• Confirm every meeting's time, attendees, link, and purpose at least 24 hours in advance
• Use Claude's calendar connector to prepare daily and weekly calendar summaries, then check them against the real calendar before they go out
• Coordinate personal appointments and travel where the placement includes it

Inbox & Communication

• Triage the inbox daily: handle routine items, draft what needs the owner's voice, and escalate what needs their decision
• Draft outbound email through Claude in the practice's brand voice and review every draft before sending
• Follow a defined escalation matrix with set response windows for urgent, same-day, and routine items
• Acknowledge email within 4 business hours and flag anything urgent to the owner within 30 minutes

Tasks, Projects, Meetings & Reporting

• Keep one task tracker current every day, covering every commitment, owner, and deadline
• Coordinate projects across the owner, staff, and vendors, breaking them into clear steps and tracking milestones through to completion
• Build meeting agendas in Claude from what's open on the tracker
• Create presentations and slide decks for the owner's meetings, trainings, and partner conversations
• Turn meeting notetaker transcripts into same-day recaps with action items assigned to the right people
• Deliver a Daily Summary and Weekly Summary so the owner never has to ask what happened
• Pull reports from the practice's CRM, EMR, or spreadsheets and spot-check the numbers before they go anywhere

Practice Coordination & Administrative Support

• Follow up with patients and clients after interactions and close the loop
• Support referrals, waitlists, and scheduling-related workflows
• Handle invoices, PTO tracking, vendor coordination, and compliance reminders
• Write and maintain SOPs for recurring work
• For practices that include it, monitor social platforms and Google and Yelp reviews, and draft responses for the owner's approval

Claude Environment

• Keep the practice's brand voice file current as the practice changes
• Bring real drafts to weekly coaching calls and refine the environment based on what's working
• Maintain strict HIPAA compliance and patient confidentiality at all times. Claude never contacts a patient or staff member without your review

Job Description

This is a remote position.

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 RESPONSIBILITIES

Calendar & Scheduling

• Manage the owner's calendar with consistent color coding, time blocking, and protected focus time
• Confirm every meeting's time, attendees, link, and purpose at least 24 hours in advance
• Use Claude's calendar connector to prepare daily and weekly calendar summaries, then check them against the real calendar before they go out
• Coordinate personal appointments and travel where the placement includes it

Inbox & Communication

• Triage the inbox daily: handle routine items, draft what needs the owner's voice, and escalate what needs their decision
• Draft outbound emai