AI-Supercharged Executive Assistant

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. Its 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 youll own the owners 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. Youll get structured Claude training from your first week weekly coaching with Rockstars role lead and a community of other EAs doing the same work.

KEY RESPONSIBILITIES

Calendar & Scheduling

• Manage the owners calendar with consistent color coding time blocking and protected focus time
  
• Confirm every meetings time attendees link and purpose at least 24 hours in advance
  
• Use Claudes 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 owners voice and escalate what needs their decision
  
• Draft outbound email through Claude in the practices 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 whats open on the tracker
  
• Create presentations and slide decks for the owners 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 practices 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 owners approval
  

Claude Environment

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

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. Youll review and send communication in a business owners 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 Rockstars 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
  

WHAT WE LOOK FOR

• Judgment: you know what to handle what to draft and what to escalate and you dont escalate out of caution
  
• Follow-through: if its not written down and tracked it isnt handled. You close every loop
  
• Discretion: you handle the owners 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 havent read. Claude makes you faster. You make it correct
  

• Competitive salary based on experience
  
• Structured Claude training including connectors reporting meeting summaries and agenda building
  
• Weekly one-on-one coaching with Rockstars role lead
  
• A private community of EAs in this role to share whats working and solve problems together
  
• Access to Rockstars playbooks and VA Academy for long-term career growth
  
• Stable full-time remote work with U.S.-based healthcare practices