Executive Personal Assistant Location: Hybrid (Massachusetts or Florida) / Remote-Friendly with flexibility for in-person needs. If based in Florida, travel to Massachusetts every 4-6 weeks (or vice versa) will be required. Must be available for in-person support as needed.
Type: Full-Time with 24/7 availability mindset
This is a rare opportunity to support a high-performing entrepreneur in real estate, private equity, and high-stakes investing. Starting with personal and lifestyle management, the role quickly expands into critical business and operations support. The ideal candidate is ambitious, emotionally intelligent, detail-oriented, and thrives in fast-paced environments-anticipating needs, taking ownership, and executing with discretion. More than an assistant, this role offers a chance to join the inner circle and help build extraordinary systems for personal and business success.
Key Responsibilities Immediate Focus - Personal & Lifestyle Management (90%)
- Manage all aspects of a fast-paced personal life, including calendars, appointments, reminders, and logistics.
- Coordinate complex domestic and international travel (flights, accommodations, itineraries, ground transport, dining).
- Source, track, and document luxury purchases (cars, watches, collectibles, fashion) with precise record-keeping.
- Liaise with vendors, household staff, and service providers; ensure seamless communication and follow-up.
- Maintain household files, inventories, and digital systems for clarity and accessibility.
- Execute personal projects, research, and concierge-style tasks with discretion.
Transition Phase - Executive & Strategic Support (scales to 50%)
- Manage scheduling and act as a gatekeeper across business and personal priorities.
- Triage emails and communications; draft and manage outbound correspondence.
- Prepare agendas, research briefs, materials, and track meeting action items.
- Handle expense tracking, receipt categorization, and coordination with financial support.
- Assist with pitch decks, documents, and spreadsheets.
- Provide operational support on real estate initiatives and document management.
- Support team building, vendor coordination, and potential investor-facing projects.
Ideal Candidate Profile - 10+ years of high-level EA/PA experience, ideally supporting founders or executives (supporting HNW/UHNW clients is preferred)
- Proven success in fast-paced, high-growth, or startup environments.
- Exceptionally responsive, adaptable, proactive, and self-directed.
- Polished with external stakeholders; approachable and collaborative internally.
- Highly skilled with Google Workspace, project/task management tools, and shared drives.
- Meticulous, discreet, emotionally intelligent.
- Approaches the role as a mission, not just a job.
Availability & Compensation - Full-time with 24/7 availability mindset.
- Must be responsive during business hours.
- Primarily remote with travel and in-person requirements.
- Competitive compensation, commensurate with experience and evolving responsibilities.
To Be Considered, Please Provide: - Current resume
- 1-3 letters of recommendation
- Professional headshot
- A brief note on why this role resonates with your energy, ambitions, and career goals
