Virtual Executive Assistant – Family Owned Business Group

Summary

We are a family-owned business group overseeing a diversified portfolio of ventures across healthcare (medical practices), luxury travel, and Broadway / live entertainment production.

Our organization supports multiple senior executives who operate at the intersection of medicine, entrepreneurship, real estate, travel, and the performing arts. We are seeking a highly proactive, detail-oriented Virtual Executive Assistant to provide executive-level administrative and operational support across the group and help streamline day-to-day execution as our businesses continue to grow.

This is a unique opportunity to work closely with leadership across multiple industries, gaining exposure to complex operations, high-level decision-making, and creative as well as clinical environments.

Responsibilities

- Manage and optimize executive calendars across multiple businesses, including coordinating meetings across time zones and balancing competing priorities
- Serve as a primary communication liaison, screening and prioritizing emails, calls, and messages to ensure timely and appropriate responses
- Coordinate travel arrangements including flights, accommodations, ground transportation, and detailed itineraries for business and personal travel
- Prepare meeting materials, agendas, briefing notes, and follow-up summaries to ensure action items are tracked and completed
- Conduct research on vendors, partners, venues, travel options, market opportunities, and industry trends to support executive decision-making
- Manage relationships with vendors and external service providers, including medical offices, travel partners, production vendors, accountants, and legal teams
- Organize and maintain digital filing systems across multiple entities, ensuring documents are secure, accessible, and well categorized
- Assist with special projects, including event coordination, content creation, process documentation, operational improvements, and cross-business initiatives
- Handle personal administrative tasks as needed to support executive productivity and work-life balance
- Dentrix

Qualifications

- 2–5 years of experience as an Executive Assistant, Virtual Assistant, or similar high-level administrative role supporting senior leaders
- Exceptional written and verbal communication skills in English, with the ability to represent executives professionally across industries
- Highly resourceful and high-agency, with a demonstrated ability to anticipate needs and solve problems independently
- Advanced proficiency with productivity tools including Google Workspace (Gmail, Calendar, Drive, Docs, Sheets), Zapier, Zoom, and project management platforms
- Strong organizational skills with experience managing complex schedules and competing priorities
- Proven track record of maintaining strict confidentiality and exercising sound judgment with sensitive information
- Reliable high-speed internet and a dedicated home office setup
- Availability to work during overlapping U.S. Eastern Time hours

Preferred Qualifications

- Experience supporting founders, physicians, or executives across multiple businesses
- Familiarity with CRM systems, expense management, invoicing, and basic bookkeeping
- Experience coordinating events, travel, or live productions
- Comfort working in both clinical / professional and creative / entertainment environments
- Bilingual capabilities (Spanish is a plus but not required)
- Experience with Notion, Hubspot and Zapier

What We Offer

- Competitive compensation commensurate with experience
- Opportunity to work directly with senior leadership across healthcare, luxury travel, and Broadway / live entertainment
- Exposure to a diversified business portfolio, not a single company role
- Flexible, remote-first work environment with an emphasis on results over hours
- Long-term growth potential for the right candidate who becomes a trusted operational partner