Personal Executive Assistant

Personal Executive Assistant
St. Cloud, Florida • Flexible Hours • 1099 Independent Contractor • $20–$25/hr

Are you a seasoned professional looking for meaningful, part-time work that draws on a lifetime of skills? Do you thrive in roles where you are genuinely needed — where your reliability, good judgment, and compassionate nature make a real difference in someone’s daily life? If so, this opportunity may be a perfect fit.

We are seeking a trusted, long-term Personal Executive Assistant to support a private individual in St. Cloud, Florida. This role requires someone who is not only highly organized and capable, but also genuinely caring — someone willing to become an essential part of daily life and operations. The individual you will support is visually impaired, and this role requires you to serve as his eyes, advocate, and organizational anchor.

This is not a corporate job. It is a human one. You will be trusted with access to personal finances, sensitive information, and real responsibility. In return, you will find a role with genuine purpose, flexibility, and longevity.

What You’ll Do

Administrative & Executive Support

• Manage email correspondence, written communications, and incoming mail
• Handle calendar management, scheduling, and appointment coordination
• Support preparation for speaking engagements and meetings
• Assist with bookkeeping and financial organization, including tax season preparation
• Manage documents and files using Microsoft Office and iOS platforms
• Assist with end-of-life planning and legal/administrative follow-through

Personal & Household Operations

• Oversee contractors and manage home improvement projects (e.g., outdoor kitchen renovations)
• Coordinate day-to-day household operations including staff, cleaning, and household logistics
• Manage and organize medications, prescription pickups, and daily medication schedules
• Drive to medical appointments, errands, and other personal engagements

Family Coordination & Life Management

• Assist with timesharing coordination and logistics for two young children
• Research and plan family trips, travel logistics, and lodging
• Identify and coordinate children’s activities and enrichment opportunities
• Serve as a consistent point of contact to keep the principal on track with daily priorities

Who We’re Looking For

This role is well-suited for a retired professional or experienced individual seeking part-time work with genuine purpose. You may have spent your career in executive support, healthcare, education, social services, or business operations — and now want a role that puts those skills to meaningful use without the demands of full-time corporate life.

You are:

• A compassionate, patient individual who takes genuine pride in supporting others
• Highly organized, proactive, and capable of managing competing priorities independently
• Discreet and trustworthy with sensitive personal and financial information
• Tech-comfortable: proficient in Microsoft Office and iOS devices
• A clear, confident communicator — in both writing and conversation
• Reliable, consistent, and committed to a long-term relationship

Requirements

• Bachelor’s degree required
• 8+ years of experience supporting an executive, business owner, or private household
• Proficiency in English
• Valid driver’s license and clean driving record
• Must pass a thorough criminal background check
• Drug-free lifestyle — no exceptions
• Strong financial responsibility; good credit history required (access to financial accounts will be granted)
• Local to St. Cloud, Florida or willing to commute

Compensation & Schedule

• $20–$25 per hour, commensurate with experience
• 1099 Independent Contractor arrangement
• Flexible 25–35 hours per week — schedule designed around your availability
• Long-term engagement with a stable, consistent principal

If you are a trustworthy, capable professional looking for work that truly matters — where your experience, compassion, and reliability are valued every single day — we would love to hear from you.