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Rockstar is hiring an AI-Supercharged Executive Assistant to support U.S.-based healthcare practice owners on a full-time remote basis. This role runs Claude AI workflows, manages calendars, inbox, tasks, and daily follow-through with HIPAA compliance and professional discretion.
You will draft, review, and send communications, and produce daily and weekly summaries for leadership. Ideal candidates have proven EA experience, strong written English, and hands-on AI tool experience.
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.
This is a remote position.
Inbox & Communication
Triage the inbox daily: handle routine items, draft what needs the owner's voice, and elevate 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
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 escal. 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 escal, and you don't escal 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.
Bring your organization, judgment, and professionalism to a role that supports senior leadership and enables business success. As an Executive Administrative Assistant, you will manage complex schedules, coordinate critical meetings, and handle travel and expenses with precision and discretion. You’ll work in a dynamic environment where priorities shift quickly and confidentiality matters. We value proactive partners who anticipate needs and deliver high‑quality support.
As an Executive Administrative Assistant within the executive leadership team, you will provide day‑to‑day administrative support to Senior Executives. You will manage complex calendars and meetings, serve as a key point of contact for communications into the executive’s office, and coordinate travel and expense processing. You will use sound judgment, handle sensitive information appropriately, and ensure smooth execution across competing priorities.
Job Responsibilities • Manage a complex calendar for Senior Executives, including prioritization, scheduling, and conflict resolution • Coordinate internal and external meetings, including logistics such as conference rooms, events, and catering • Screen and route incoming calls and requests, prioritizing appropriately and exercising discretion when sharing information • Respond to and follow up on inquiries on behalf of the executive, ensuring timely and professional communication • Coordinate domestic and international travel, maintaining detailed itineraries and trip logistics • Prepare, reconcile, and submit expense reports accurately and on time in accordance with applicable policies • Serve as a point of contact for internal stakeholders, clients, and visitors interacting with the executive’s office • Support day‑to‑day administrative needs and help resolve scheduling or logistics issues as they arise
Required Qualifications, Capabilities, and Skills • Experience providing administrative support to senior leaders in a fast‑paced environment • Strong organizational skills with the ability to manage multiple priorities and last‑minute changes • Strong attention to detail and ability to execute tasks accurately under time pressure • Strong written and verbal communication skills with professional etiquette • Demonstrated ability to handle sensitive information with discretion and sound judgment • Proficiency in Microsoft Outlook and experience scheduling complex meetings • Ability to work collaboratively with stakeholders at all levels • Strong follow‑up skills and a proactive, service‑oriented mindset
Preferred Qualifications, Capabilities, and Skills • Experience supporting executive‑level leaders or managing high‑volume calendars • Experience coordinating international travel and complex itineraries • Experience using expense management tools (., SAP Concur or similar) • Experience coordinating events, town halls, or large meetings
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Your key responsibilities include
Skills and attributes for success
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What we look for
We’re interested in knowledgeable professionals ready to take ownership for attracting and engaging external candidates for EY. You’ll need to be naturally curious, ready to learn and have a genuine passion for finding the right people for the right roles.
What working at EY offers
We offer a competitive compensation package where you’ll be rewarded based on your performance and recognized for the value you bring to our business. In addition, our Total Rewards package includes medical and dental coverage, both pension and 401(k) plans, a minimum of 18 days of paid time off with additional time based on your level and years of service plus 12 observed holidays, and a range of programs and benefits designed to support your physical, financial and social well‑being.
About EY
As a global leader in assurance, tax, transaction and advisory services, we hire and develop the most passionate people in their field to help build a better working world. This starts with a culture that believes in giving you the training, opportunities and creative freedom to make things better.
**Location** Av. Madero 1250, Retiro, ., Buenos Aires Buenos Aires 1104, Argentina
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