AI-Supercharged Executive Assistant

About the role

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