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 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
Requirements
Required
Proven experience as an Executive Assistant, Administrative Assistant, or similar role supporting a business owner or leader
Hands-on experience using AI tools for real work
Strong project coordination and task management skills, with a track record of moving work from assigned to done
Excellent time management and the ability to prioritize competing deadlines without dropping anything
Strong presentation skills, including building clear, polished slide decks
Excellent written English. You'll review and send communication in a business owner's voice every day
Strong judgment about what to handle on your own and what to escalate
Comfort working in Google Workspace or Microsoft 365
Ability to work independently and keep steady communication with the practice owner
Willingness to complete Rockstar's confidentiality and compliance training before your start date
Reliable home office setup with a stable internet connection suitable for HIPAA-compliant remote work
Preferred
Experience with ChatGPT and Claude
Experience in the healthcare industry, especially outpatient practices such as physical therapy, occupational therapy, or speech therapy
Experience with Canva
Familiarity with HIPAA and handling patient information
Familiarity with EMR platforms such as Prompt, WebPT, or Raintree, or CRMs such as HubSpot or Zoho
Experience with project management tools such as Asana or Monday.com
WHAT WE LOOK FOR
Judgment: you know what to handle, what to draft, and what to escalate, and you don't escalate out of caution
Follow-through: if it's not written down and tracked, it isn't handled. You close every loop
Discretion: you handle the owner's information and patients' information with care, and only share it with the people who need it
Curiosity: you want to get better at running AI, and you bring real drafts and real questions to coaching every week
Ownership: you never send a draft you haven't read. Claude makes you faster. You make it correct
Benefits
Competitive salary based on experience
Structured Claude training, including connectors, reporting, meeting summaries, and agenda building
Weekly one-on-one coaching with Rockstar's role lead
A private community of EAs in this role to share what's working and solve problems together
Access to Rockstar's playbooks and VA Academy for long-term career growth
Stable, full-time remote work with U.S.-based healthcare practices
Originally posted on Himalayas
Who can apply
Eligible countries: United States. Accepted UTC offsets: UTC-10, UTC-9, UTC-8, UTC-7, UTC-6, UTC-5, UTC+14. Review the full description for employer-specific work authorization, residency and schedule requirements.