Personal Assistant

StevenDouglas; Winter Park (FL); Hybrid; USD 24,000 - 42,000; Part time

Job summary

StevenDouglas is seeking a highly organized Personal Assistant in the Winter Park, FL area for part-time hybrid/remote support to a private individual. The role focuses on keeping schedules and life organized, while building a warm, trusted relationship with the client.

The position is flexible and part-time, with potential growth as needs evolve, and requires local availability for in-person support. Ideal candidates will be proactive, discreet, and tech-savvy, comfortable managing calendars,

Qualifications

• Must be highly organized and proactive.
• Excellent written and verbal communication.
• Discretion and trustworthiness with personal matters.
• Ability to manage multiple calendars and travel plans.

Responsibilities

• Manage personal and professional calendars, appointments, reminders, important dates, and deadlines.
• Coordinate travel itineraries including flights, hotels, and ground transportation.
• Handle personal email, correspondence, and routine responses; organize mail.
• Assist with household management, errands, shopping, and wardrobe-related tasks.

Skills

Calendar management

Email handling

Travel coordination

Discretion

Communication

Tech-savvy

Job description

We are seeking a highly organized, proactive, and personable Personal Assistant to provide day-to-day support to a private individual based in Winter Park, Florida.

The position can begin on a part-time basis, with the opportunity to evolve as the relationship and needs develop. This is a particularly appealing opportunity for someone looking for a flexible role that combines traditional personal assistance with a highly personable, relationship-driven working environment.

The right individual will become a trusted and valued presence in the client’s day-to-day life — someone who keeps things organized and running smoothly, but is also warm, engaging, intuitive, and genuinely enjoys building a strong working relationship with the person they support.

This is a hybrid/remote position; however, candidates must live locally in the Winter Park/Greater Orlando area and be readily available for in-person support as needed.

Key Responsibilities

Calendar, Appointments & Correspondence

• Manage personal and professional calendars, appointments, reminders, important dates, and deadlines.
• Manage email and correspondence, draft routine responses, organize mail, and flag matters requiring attention.
• Coordinate medical, dental, grooming, and other personal appointments.

Travel & Personal Organization

• Coordinate flights, hotels, transportation, restaurants, activities, and detailed travel itineraries.
• Organize travel documents, passports, confirmations, luggage, packing/unpacking, and ensure travel essentials are stocked and ready.
• Maintain organized digital and physical files for important personal and travel documents.

Home & Lifestyle Management

• Coordinate household staff, vendors, maintenance, repairs, deliveries, contractors, and service appointments.
• Handle personal errands, returns/exchanges, prescriptions, meal delivery services, and other day-to-day needs.
• Assist with personal shopping, wardrobe needs, dry cleaning, alterations, and preparation for trips and events.

Vehicle Management

• Coordinate vehicle servicing, maintenance, detailing, and other automotive needs.

Special Occasions & Gifting

• Keep track of birthdays, anniversaries, and other important occasions.
• Coordinate gifts, flowers, cards, and deliveries throughout the year.

Ideal Candidate

• Highly organized, intelligent, resourceful, and proactive, with excellent follow-through.
• Warm, personable, engaging, and someone who naturally builds strong relationships.
• Strong written and verbal communication skills with a polished, professional demeanor.
• Discreet, trustworthy, and comfortable handling confidential and personal matters.
• Tech-savvy and comfortable managing calendars, email, travel, digital files, and online purchases.
• Flexible and willing to assist with a variety of needs as they arise.
• Prior experience supporting a private individual, family, family office, or UHNW household is preferred.
• Comfortable supporting a principal who is actively involved in philanthropic, charitable, and community organizations.

Work Arrangement

This is a hybrid/remote role based in Winter Park, Florida and can begin on a part-time basis. While many responsibilities can be handled remotely, the Personal Assistant must be local and available to provide hands-on support in Winter Park as needed.

There is flexibility around how the position is structured initially, making this an excellent opportunity for the right individual to establish a strong working relationship with the principal and potentially grow the role over time.