Top 51 Chauffeurs Jobs in Medford, Ma

Private Chauffeur / Personal Assistant
DJ Estates —Winchester, MA
- $80,000 - $100,000 a year
- Weekends as needed
- Background check
- Mid-level
- Driver's License
- Health insurance
- 401(k)
Quick Apply
9d
Chauffeur Driver
IQ Boston Transport Inc —Boston, MA
- $23 - $35 an hour
- Weekends as needed
- Clean driving record
- Local
- Mid-level
Quick Apply
CDL Driver - With Passenger and Air Brake Endorsements
DPV Transportation Worldwide —Waltham, MA
- From $28 an hour
- Full-time
- CDL B
- Background check
- Clean driving record
- Paid holidays
- Health insurance
Quick Apply
2d
CDL Driver - Class B with Passenger Endorsement
DPV Transportation Worldwide —Cambridge, MA
- $25 an hour
- Full-time
- Background check
- Clean driving record
- Mid-level
- Paid holidays
- Health insurance
Quick Apply
2d
CDL Driver - Class B with Passenger & Air Brake Endorsement
DPV Transportation Worldwide —Braintree, MA
- $25 - $28 an hour
- Full-time
- CDL B
- Background check
- Clean driving record
- Paid training
- Paid holidays
Quick Apply
4d
Customer Delivery Driver 4- day work week!
Carvana —Framingham, MA
- $24 - $26 an hour
- Clean driving record
- Ability to walk for extended periods
- DOT physical examination
- Wellness program
- Employee stock purchase plan
Weekend CDL Charter Driver
DPV Transportation Worldwide Inc —Waltham, MA
- $35 - $40 an hour
- Overtime
- Customer service
- Mid-level
- CDL
- Health insurance
- Dental insurance
Quick Apply
2d
Customer Service Delivery Advocate 4- day work week!
Carvana —Boston, MA
- $24 - $26 an hour
- Clean driving record
- Ability to walk for extended periods
- DOT physical examination
- Wellness program
- Employee stock purchase plan
Quick Apply
Customer Delivery Specialist 4- day work week!
Carvana —Marlborough, MA
- $24 - $26 an hour
- Clean driving record
- Ability to walk for extended periods
- DOT physical examination
- Wellness program
- Employee stock purchase plan
Quick Apply
Food Delivery Driver
Uber Drivers —Holbrook, MA
- Part-time
- Background check
- Local
- Driver's License
Deliver Food with Uber - Flexible Gig
Uber Drivers —Lowell, MA
- Part-time
- Background check
- Local
- Driver's License
Flexible Schedule - Deliver with Uber Eats
Uber Drivers —Rockland, MA
- Part-time
- Background check
- Local
- Driver's License
- Flexible schedule
Driver
Uber Drivers —Lynn, MA
- Part-time
- Background check
- Local
- Driver's License
10d
Customer Service Delivery Advocate
Carvana —Brockton, MA
- $22 - $24 an hour
- Clean driving record
- Ability to walk for extended periods
- DOT physical examination
- Wellness program
- Employee stock purchase plan
Quick Apply
Subcontractor Driver – Elite School Car Account (Boston Metro Area)
Master Livery Service Corp. —Boston, MA
- From $1,250 a week
- Contract
- Background check
- Mid-level
Quick Apply
CHAUFFEUR
DPV TRANSPORTATION INC —Everett, MA
- From $25 an hour
- Overtime
- Background check
- Clean driving record
- Mid-level
- Paid holidays
- Health insurance
Quick Apply
Executive Protection Driver
Control Risks —Boston, MA
- $100,000 - $115,000 a year
- Weekends as needed
- Hybrid work
- CPR Certification
- Clean driving record
- Military
- AD&D insurance
- Health insurance
Quick Apply
Professional Chauffeur
United Private Car —Hyde Park, MA
- From $22 an hour
- Part-time
- Background check
- Pass drug screening
- Mid-level
Quick Apply
Driver
The Salvation Army Eastern Territory —Canton, MA
- $15 - $20 an hour
- On call
- High school diploma or GED
- Ability to lift 50 pounds
- Driver's License
- AD&D insurance
- Paid holidays
CDL Chauffeur
Carey International —Braintree, MA
- $17 an hour
- Full-time
- CDL B
- Clean driving record
- Writing skills
Quick Apply

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Private Chauffeur / Personal Assistant

DJ Estates
Winchester, MA

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Job Details

Full-time
$80,000 - $100,000 a year
9 days ago

Benefits

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

Qualifications

Computer operation
Driver's License
Traffic condition navigation
Navigation systems
Computer skills
Managing executive calendars
Mobile devices

Full Job Description

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

Quick Apply

Refine Your Search

chauffeurs jobs in medford, ma

Private Chauffeur / Personal Assistant

Chauffeur Driver

CDL Driver - With Passenger and Air Brake Endorsements

CDL Driver - Class B with Passenger Endorsement

CDL Driver - Class B with Passenger & Air Brake Endorsement

Customer Delivery Driver 4- day work week!

Weekend CDL Charter Driver

Customer Service Delivery Advocate 4- day work week!

Customer Delivery Specialist 4- day work week!

Food Delivery Driver

Deliver Food with Uber - Flexible Gig

Flexible Schedule - Deliver with Uber Eats

Driver

Customer Service Delivery Advocate

Subcontractor Driver – Elite School Car Account (Boston Metro Area)

CHAUFFEUR

Executive Protection Driver

Professional Chauffeur

Driver

CDL Chauffeur

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