Executive/Personal Assistant

Dunedin, FL

Executive/Personal Assistant (Hybrid) - Dunedin, FL

Location: Dunedin, Florida (Hybrid; Travel Required)

Compensation: Based on experience

Benefits: Health insurance and full benefits package

Schedule: Monday–Friday, primarily morning through afternoon support; must have a true 24/7 mindset. While the core schedule is weekdays, urgent tasks may arise during evenings or downtime and require responsiveness.

Position Overview

A driven entrepreneur based in Dunedin, Florida is seeking a highly capable Executive / Personal Assistant to serve as a trusted right hand across both professional and personal matters. This is a high-trust role for a confident, organized, and assertive professional who thrives in fast-paced environments, manages constant urgency, and is comfortable holding principal accountable. The principal oversees multiple companies, works in high-profile spaces, attends major charitable and PR events, and travels frequently—often last minute via private aviation. She is seeking someone who can take ownership, push priorities forward, and ensure balance by prompting movement, meals, and follow-through. This role blends executive support, personal accountability, and project management. The ideal candidate is comfortable operating as both strategist and executor and is unfazed by urgency, visibility, or scale. The position may begin hybrid and evolve into more in-person support over time.

Key Responsibilities

Executive Support

Manage and reconcile multiple complex calendars across several businesses; anticipate conflicts, prevent missed commitments, and prioritize effectively
Coordinate frequent, often last-minute domestic and international travel (New York, Las Vegas, international cruising, major sporting events), primarily via private aviation
Act as a strategic gatekeeper — filtering noise, triaging urgent requests, and keeping the principal focused on priorities
Support PR and public-facing obligations, including coordination with PR firms, charity partners, and event organizers
Assist with preparation and appear for public appearances, charitable events, and on-stage presentations

Personal & Lifestyle Support (In-Person Focus)

Keep the principal organized, accountable, and moving — including prompting her to attend workouts, eat meals, take breaks, and step away from her computer
Manage and schedule personal appointments, including dental care, medical providers, and international health-related travel
Support day-to-day personal logistics and errands as needed
Assist with oversight of an upcoming home renovation project
Help maintain structure during periods of intense workload and frequent travel

Financial & Administrative Oversight

Execute and track wire transfers and payments
Organize contracts, records, and sensitive documents across multiple companies
Coordinate with accounting, tax, and legal partners
Ensure deadlines, renewals, and obligations are met across all entities

Household & Family Context

Two children: a 7-year-old daughter and a 16-year-old son (no childcare or driving responsibilities required)
Household includes two dogs and two cats (no walking/petcare involved)
The principal is purchasing multiple properties; relocation support is available if needed, including a condo for a single candidate or a home suitable for a family, located near good schools

Ideal Candidate Profile

7+ years of experience as an Executive Assistant, Personal Assistant, or hybrid EA/PA supporting a founder, senior executive, or UHNW individual
Highly organized, proactive, and calm under pressure
Confident, assertive, and comfortable pushing back — able to tell a driven principal when to move, pause, or delegate
Exceptional judgment and discretion with sensitive personal, financial, and business matters
Thrives in environments with constant urgency and shifting priorities
Comfortable with frequent, last-minute travel and non-traditional workflows
Tech-savvy and adept at managing multiple systems and calendars
Willing to be deeply embedded in both professional and personal aspects of the principal’s life

Additional Notes

Hybrid role with flexibility; executive tasks may be handled remotely initially, with personal duties requiring in-person presence
Travel is frequent but optional for certain events; the assistant is welcome but not required to attend all engagements
Long-term growth potential, including expansion into broader operational oversight or leadership of an EA/PA team

This role is ideal for someone who wants to operate at a high level of trust and responsibility, make a tangible daily impact, and support a powerful, fast-moving principal who genuinely needs — and values — strong partnership.