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 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

This is a remote position.

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 elevate
- 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 Hub Spot or Zoho
- Experience with project management tools such as Asana or Monday

WHAT WE LOOK FOR

- Judgment: you know what to handle, what to draft, and what to elevate, and you don't elevate 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

Job Summary: The Talent Innovation & Analytics (TIAT) Team is seeking an experienced portfolio and project management professional with strong business consulting, strategic planning, governance, and stakeholder management capabilities. This role oversees portfolio management, intake and prioritization, resource and capacity planning, governance, and delivery oversight for strategic Talent initiatives across the United States.
The successful candidate will serve as a senior advisor to Talent stakeholders and TIAT team members, translating business demand into a prioritized, actionable portfolio. The role will provide visibility into priorities, capacity, risks, and dependencies; support informed investment and resource decisions; and establish consistent processes and operating rhythms that enable effective execution.

This position requires strong business acumen, portfolio and project management expertise, problem-solving, executive communication, relationship management, and technical fluency. The role will collaborate across and international teams to strengthen portfolio transparency and accountability while enabling initiatives that drive innovation, efficiency, transformation, and measurable business value.

Key Functions and Responsibilities
I. Portfolio Strategy & Governance

- Manage the TIAT portfolio to ensure initiatives remain aligned with organizational priorities, available capacity, and expected business value.
- Establish and facilitate portfolio governance, prioritization reviews, and operating rhythms that enable transparency, consistency, accountability, and timely decision-making.
- Develop and maintain portfolio roadmaps, capacity plans, prioritization frameworks, and executive reporting that provide visibility into project health, resources, risks, dependencies, and value realization.
- Balance strategic value, innovation, operational needs, capacity, risk, and delivery feasibility when informing portfolio recommendations and trade-offs.

II. Intake & Demand Management

- Manage the end-to-end intake and demand process for analytics, automation, AI, technology, and process transformation requests.
- Facilitate discovery with stakeholders to understand business problems, desired outcomes, requirements, risks, and opportunities.
- Evaluate and prioritize requests based on strategic alignment, expected value, feasibility, complexity, resource requirements, risk, and delivery capacity.
- Translate complex or ambiguous business needs into clearly defined opportunities, requirements, roadmaps, and delivery plans.

III. Project Delivery & Capacity Management

- Oversee multiple concurrent projects and workstreams, monitoring timelines, milestones, resources, quality, risks, dependencies, and stakeholder expectations to support successful delivery.
- Coordinate workload planning, prioritization, and capacity management across project management and ringfenced technical resources, balancing business priorities with delivery commitments.
- Establish and maintain consistent project management standards, governance practices, reporting expectations, and delivery methodologies across the portfolio.
- Proactively address risks, issues, dependencies, and capacity constraints while continuously improving delivery processes to strengthen quality, efficiency, predictability, and stakeholder experience.

IV. Business Consulting & Technology Enablement

- Serve as a strategic advisor to Talent stakeholders, helping identify opportunities for innovation, process improvement, analytics, automation, AI, and technology-enabled transformation.
- Facilitate workshops, process reviews, and stakeholder discussions to challenge assumptions, clarify business needs, evaluate options, and shape practical recommendations.
- Partner with business and technical teams to translate requirements into functional solution designs and scalable delivery approaches that meet quality, security, governance,



adoption, and operational requirements.
- Develop business cases, recommendations, project charters, implementation roadmaps, process documentation, governance standards, adoption plans, and executive-ready communications supporting successful decision-making and implementation.

V. Stakeholder Partnership & Continuous Improvement

- Build and maintain trusted relationships across Talent, the Talent Enablement Center, Virtual Talent Hub, reporting and analytics teams, project resources, technical delivery teams, and other key stakeholders.
- Synthesize complex portfolio and project information into clear, decision-oriented insights and recommendations for senior stakeholders.
- Promote effective collaboration, accountability, knowledge sharing, and continuous learning across project and delivery teams.
- Continuously assess and enhance portfolio, project, and delivery practices to increase efficiency, strengthen execution, improve stakeholder experience, and maximize business value.

Knowledge and Skills Requirements:

- Advanced knowledge of portfolio, program, and project management, including intake, prioritization, governance, demand management, capacity planning, risk management, and resource planning.
- Ability to partner across business and technical teams to connect strategic priorities with delivery capacity, translating business needs into solutions across analytics, automation, AI, technology, and process transformation.
- Strong business consulting and analysis capabilities, including requirements gathering, stakeholder discovery, process analysis, documentation, solution evaluation, and roadmap development.
- Demonstrated ability to connect organizational priorities to portfolio decisions, resource allocation, sequencing, and investment recommendations.
- Experience establishing and maintaining portfolio governance, project management standards, reporting practices, and delivery methodologies.
- Strong analytical capabilities with the ability to synthesize complex project, portfolio, capacity, and business information into actionable insights and recommendations.
- Strong understanding of Agile and Waterfall delivery methodologies, including project planning, testing, deployment, change management, and adoption.
- Ability to understand complex business and technical needs and partner with technical resources to shape practical, scalable solutions.
- Strong executive presence, written and verbal communication, facilitation, and presentation skills, with the ability to influence stakeholders and drive decisions.
- Demonstrated ability to manage multiple competing priorities, risks, dependencies, and workstreams while maintaining organizational alignment.
- Strong relationship management skills with experience working across cross‑functional, general, and distributed teams.
- Knowledge of Talent and HR processes, workforce strategy, people analytics, and HR technology preferred.
- Strong organizational skills, attention to detail, judgment, and ability to operate effectively in complex and ambiguous environments.

Other Technical Requirements:

- Working knowledge of Microsoft Power Platform (Power BI, Power Apps, Power Automate Online, Power Pages), with the ability to evaluate potential applications and collaborate effectively with technical teams.
- Familiarity with Microsoft Copilot, Copilot Studio, AI-enabled productivity tools, agentic AI concepts, or similar technologies.
- Experience with HR technologies such as Workday, Success Factors, People Soft, Taleo, or similar systems preferred.
- Experience with business intelligence, workflow automation, reporting, collaboration platforms, and data visualization tools.

Job Requirements:

Education

- Bachelor’s degree in Business, Information Systems, Analytics, Data Management, Computer Science, Project Management, or a related field required.
- PMP, PgMP, Agile, Scrum, SAFe, or equivalent certification preferred.

Experience

- 8+ years of progressive project, program, or portfolio management experience.
- 5+ years leading project teams and managing complex portfolios.
- Experience managing both business and technical initiatives.
- Experience operating within PMO and governance structures.
- Experience leading global or distributed teams.
- Experience supporting technology, analytics, automation, AI, or transformation programs.

What Success Looks Like in Year One:

- Improved portfolio visibility, governance, and executive reporting.
- Implemented effective capacity planning across project management and Ringfence resources.
- Increased project throughput while strengthening delivery quality and predictability.
- Established consistent portfolio and project management practices that strengthen accountability and execution.
- Enabled scalable delivery of Innovation & Analytics services across TEC and Talent.
- Developed a sustainable operating model that effectively balances strategic demand, technical capacity, risk, and business value.

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