Private Chauffeur / Personal Assistant

Location: Winchester, MA / Greater Boston

Job Type: Full-time, long-term

Pay: $80,000–$100,000 per year

Benefits

401(k), health insurance, paid time off

We are seeking an exceptional Private Chauffeur & Personal Assistant to support a private principal and family in the Greater Boston area.

This is a highly trusted, driving-first position requiring professionalism, discretion, sound judgment, and a genuine commitment to service. The successful candidate will become an integral part of a private family office, providing private transportation, personal assistance, and logistical support while maintaining complete confidentiality.

This is intended to be a long-term position. We are seeking a dependable professional who wants to build a trusted, lasting working relationship with the principal and family—not a short-term or transitional role.

Schedule and availability

This is a full-time position averaging approximately 45–55 hours per week. The chauffeur will support transportation surrounding the principal's work schedule, including preparation and end-of-day travel.

The role also requires flexibility for early mornings, evenings, weekends, occasional holidays, airport runs, special events, overnight travel, and extended trips. The ability to accommodate last-minute schedule changes is essential. Candidates seeking a traditional Monday–Friday, 9-to-5 schedule are unlikely to find this role a good fit.

Responsibilities

Private chauffeur

• Safely and professionally transport the principal to appointments, meetings, airports, restaurants, events, and other destinations.
• Provide transportation for family members and guests as requested.
• Plan efficient routes; monitor traffic, weather, flight changes, and other travel conditions.
• Arrive early, confirm trip details, and adapt calmly to changing schedules.
• Create a quiet, comfortable passenger experience and assist with luggage, packages, and related needs.

Vehicle management

• Maintain all assigned vehicles in exceptional, road-ready, presentation-ready condition.
• Coordinate fueling, cleaning, detailing, inspections, maintenance, repairs, registration, and supplies.
• Track maintenance records and service schedules; proactively address vehicle needs.

Personal assistance and household support

• Run personal and business errands; manage deliveries, package returns, dry cleaning, tailoring, and light wardrobe-related coordination.
• Coordinate appointments, reservations, travel arrangements, itineraries, and calendar logistics.
• Coordinate vendors, contractors, household maintenance appointments, and event preparation.
• Handle confidential documents and sensitive information with complete discretion.
• Support day-to-day household logistics, special projects, and other executive-support responsibilities as assigned.

Who we’re looking for

The right person naturally enjoys supporting others and finds satisfaction in making each day easier, more organized, and less stressful. You notice details without being asked, anticipate needs, solve problems quietly, and take pride in consistent, reliable execution.

You are punctual, humble, organized, calm under pressure, and comfortable operating independently. Whether that means having the vehicle ready before it is needed, remembering a preference, handling an urgent errand, or preparing for tomorrow before today has ended, you bring thoughtful and professional service to every task.

Qualifications

• Exceptional, safe, and confident driving skills, with a valid driver’s license and excellent driving record.
• Comfort driving throughout Greater Boston, navigating traffic, planning routes, and handling extended trips.
• Prior private chauffeur or executive-driving experience is welcome but not required. We are open to candidates with strong judgment, a polished service mindset, and a genuine willingness to learn the standards of a private chauffeur role.
• Exceptional integrity, discretion, professionalism, and sound judgment.
• Strong organization, communication, navigation, calendar, and basic computer skills.
• High attention to detail, initiative, flexibility, and ability to remain calm under pressure.
• Comfortable using smartphones, GPS navigation, scheduling software, and basic computer applications.
• Ability to lift up to 40 pounds.
• Authorization to work in the United States.

Finalists must successfully complete a motor-vehicle-record review, professional-reference checks, and a background check as permitted by applicable law.

Pay: $80,000.00 - $100,000.00 per year

Benefits

• 401(k)
• Employee discount
• Health insurance
• Paid time off
• Retirement plan

Application Question(s)

• Why are you interested in a long-term Private Chauffeur & Personal Assistant position?
• What compensation range are you seeking within the posted $80,000–$100,000 range?
• What days and hours are you available to work?
• When can you start?

Work Location: In person