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Chauffeur Driver / Assistant

DJ Estates
Winchester, MA Full Time
POSTED ON 11/28/2025 CLOSED ON 12/26/2025

What are the responsibilities and job description for the Chauffeur Driver / Assistant position at DJ Estates?

We are seeking a professional, discreet, and service-oriented Executive Chauffeur & Personal Assistant to provide safe, reliable transportation for a private family and their business associates in the Boston area.

When not driving, this role includes personal assistant and household support duties, helping ensure the principal’s day-to-day life runs smoothly. The ideal candidate will demonstrate exceptional professionalism, attention to detail, and flexibility, with the ability to perform effectively in all weather conditions while maintaining strict confidentiality.

Responsibilities

  • Safely transport the principal, family members, and guests to personal, social, and business engagements.
  • Maintain flexibility for some early mornings, evenings, and weekends as needed.
  • Deliver a comfortable, courteous, and confidential travel experience.
  • Clean, fuel, and maintain luxury vehicles in top condition; coordinate detailing and service appointments.
  • Perform snow removal, shoveling, and salting around vehicles, walkways, and driveways for safe travel during winter months.
  • Assist with personal errands, deliveries, and scheduling when not driving.
  • Greet passengers professionally, assist with doors, luggage, and umbrellas during inclement weather.
  • Plan efficient routes, adjusting for traffic and weather conditions.
  • Communicate effectively with household and office staff to coordinate logistics.
  • Maintain absolute confidentiality and demonstrate sound judgment at all times.

Qualifications

  • Minimum 5 years of professional driving experience, preferably with private families or executives.
  • Clean driving record and valid Massachusetts driver’s license.
  • Experience driving large and executive-class vehicles.
  • Strong knowledge of Boston-area routes, airports, and traffic patterns.
  • Experience providing personal assistant or office support preferred.
  • Ability to perform physical tasks (e.g., snow removal, shoveling, luggage handling).
  • Must pass a comprehensive background check and drug screening.

Key Traits

  • Professional and polished appearance.
  • Reliable, punctual, and detail-oriented.
  • Calm and adaptable under pressure.
  • Discreet, loyal, and respectful of privacy.
  • Service-driven with a focus on excellence.

Compensation & Benefits

  • Compensation depends on experience and skillset.
  • Company vehicle provided for work duties.

Job Type: Full-time

Pay: $50,000.00 - $80,000.00 per year

Benefits:

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

Application Question(s):

  • What days and times are you available to work as a chauffeur/assistant?
  • Describe your driving experience in rain and snow.
  • When can you start?
  • What do you expect for pay?

Work Location: In person

Salary : $50,000 - $80,000

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