Executive/Personal Assistant

The Wellington Agency • Dunedin, FL

8h • Hybrid

About The Position

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.

Requirements

• 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
• Must have a true 24/7 mindset. While the core schedule is weekdays, urgent tasks may arise during evenings or downtime and require responsiveness.

Responsibilities

• 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
• 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
• 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

Benefits

• Health insurance
• Full benefits package
• Relocation support is available if needed, including a condo for a single candidate or a home suitable for a family, located near good schools

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed