Traveling Private Driver | Palm Beach + Lake Geneva Job at Oceanside Staffing, Palm Beach, FL

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  • Oceanside Staffing
  • Palm Beach, FL

Job Description

A private family in Palm Beach is seeking an experienced Traveling Private Driver to provide safe, discreet, and highly professional transportation for the principal and family.

This is a full-time, year-round position based in Palm Beach, with seasonal travel to the family’s residence near Lake Geneva, Wisconsin for 6-8 weeks each year. Accommodations are provided while working in Wisconsin.

The ideal candidate is a polished private service professional with significant experience driving UHNW principals and an impeccable driving record . This individual understands that exceptional private driving goes far beyond getting from one destination to another. Punctuality, discretion, anticipation, route planning, vehicle presentation, and an unwavering commitment to safety are essential.

We are looking for someone flexible, dependable, and service-minded who understands the changing demands of a private household and is comfortable adapting their schedule around the needs of the principals.

Key Responsibilities


Principal & Family Driving

  • Provide safe, discreet, and professional transportation for the principals, family members, and guests
  • Drive throughout Palm Beach, South Florida, and surrounding areas as required
  • Provide transportation while the family is in residence near Lake Geneva, Wisconsin
  • Complete airport transfers and transportation to appointments, meetings, dinners, events, shopping, and other personal engagements
  • Anticipate routes, traffic patterns, construction, weather conditions, and potential delays to ensure timely arrivals
  • Maintain excellent knowledge of local routes and utilize navigation and traffic-monitoring tools appropriately
  • Assist principals and guests with doors, luggage, packages, and belongings as appropriate
  • Remain available and prepared during appointments, events, dinners, and other engagements when required
  • Maintain the highest level of discretion, professionalism, and confidentiality at all times

Vehicle Management

  • Ensure all family vehicles are impeccably clean, fueled, stocked, and ready for use
  • Conduct routine vehicle checks and immediately communicate any maintenance or safety concerns
  • Coordinate scheduled maintenance, repairs, detailing, inspections, registrations, and other vehicle-related services
  • Maintain accurate vehicle records and monitor upcoming service requirements
  • Keep vehicles stocked with the principals’ preferred supplies and amenities
  • Coordinate with appropriate household team members regarding vehicle technology, tracking systems, and installations
  • Ensure vehicles are properly prepared for seasonal use and changing weather conditions in both Florida and Wisconsin

Errands & Household Support

  • Complete personal and household errands between driving assignments
  • Assist with airport luggage, packages, deliveries, and other transportation-related needs
  • Complete grocery, pharmacy, supply, and other household pickups as requested
  • Transport family pets to veterinary, grooming, or boarding appointments when needed
  • Coordinate closely with the Estate Manager and household team regarding daily schedules and transportation needs
  • Assist with additional service-oriented tasks when driving responsibilities allow

Travel Requirements

Palm Beach will remain the home base for this position; however, flexibility to travel is an essential requirement of the role.

The family spends up to approximately three months each year near Lake Geneva, Wisconsin , and the Driver will be expected to travel with or join the household for 6-8 weeks during the summer.

Accommodations are provided in the Lake Geneva area while traveling for the position.  Candidates should be comfortable transitioning between the family’s residences and adapting their schedules based on the principals’ travel and occupancy.

Ideal Candidate

  • Significant professional experience as a Private Driver, Chauffeur, Executive Driver, or similar role supporting UHNW individuals or families
  • Proven experience driving UHNW principals with strong professional references
  • Impeccable driving record
  • Exceptional commitment to passenger safety and defensive driving
  • Professional, polished, discreet, and service-oriented
  • Calm and confident behind the wheel in varying traffic, weather, and road conditions
  • Excellent route planning, navigation, and time-management skills
  • Highly punctual, dependable, and organized
  • Able to anticipate the principals’ needs without being intrusive
  • Comfortable maintaining luxury and high-end vehicles
  • Strong understanding of professional driver etiquette and appropriate boundaries within a private household
  • Excellent communication skills and ability to coordinate effectively with principals and household staff
  • Flexible and adaptable to changing schedules, travel plans, and household needs
  • Comfortable around dogs and willing to assist with pet transportation as needed
  • Seeking a long-term opportunity within a professional private household

Requirements

  • Valid driver's license and impeccable driving record required
  • Professional driving experience supporting UHNW principals required
  • Strong professional references specifically related to private/UHNW driving required
  • Ability to successfully complete a comprehensive background check, motor vehicle record check, and reference verification
  • Ability and willingness to travel to Lake Geneva, Wisconsin for up to 6-8 weeks annually
  • Flexibility to work evenings, weekends, holidays, and extended hours when required
  • Ability to maintain absolute discretion and confidentiality

Compensation & Benefits

  • Starting at $40/hour, depending on experience
  • Overtime paid at time and a half (1.5x)
  • Full medical benefits
  • 401(k)
  • 10 days paid time off
  • Company-paid holidays, with flexibility when holidays cannot be observed on the actual holiday
  • Staff vehicle provided for work-related driving
  • Accommodations provided while working near Lake Geneva, Wisconsin

Schedule & Flexibility

This is a full-time, year-round, live-out position with Palm Beach serving as the Driver’s home base.

The schedule will generally follow Monday through Friday but will fluctuate based on the principals’ needs, travel, events, and guest schedules. Hours may regularly exceed 40 per week during busy periods, with overtime paid at time and a half.

Evening, weekend, and holiday availability will be required as needed. The successful candidate must be comfortable with the flexibility that comes with working in a private household and able to adapt professionally as plans change.

Travel to the family’s Lake Geneva residence is an important component of the position and may total up to 6-8 weeks each year .

Right Fit For You?

This position is ideal for an experienced Private Driver who takes genuine pride in providing safe, seamless, highly professional service. You anticipate rather than react, remain calm when plans change, keep vehicles impeccably maintained, and understand how to be attentive without being intrusive.

If you're seeking a long-term opportunity with a professional private household and enjoy working as part of a collaborative estate team, we'd love to hear from you.

Job Tags

Full time, Summer work, Seasonal work, Live out, Local area, Immediate start, Monday to Friday, Flexible hours, Weekend work, Afternoon shift

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