[Hiring] AI-Supercharged Executive Assistant @Rockstar

Role 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, built for an experienced executive assistant who wants to run AI inside a real business.

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.

Qualifications

• 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
• Excellent written English
• Strong judgment about what to handle on your own and what to escalate
• Comfort working in Google Workspace or Microsoft 365
• Strong organizational skills and consistent follow-through across a high volume of tasks
• 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

Requirements

• Experience with Claude specifically (preferred)
• Experience supporting U.S.-based outpatient healthcare practices such as physical therapy, occupational therapy, or speech therapy (preferred)
• Familiarity with HIPAA and handling patient information (preferred)
• Familiarity with EMR platforms such as Prompt, WebPT, or Raintree, or CRMs such as HubSpot or Zoho (preferred)
• Experience with project management tools such as Asana or Monday.com (preferred)

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