Executive Personal Assistant - MA & FL

Chestnut Hill, MA

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