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