A private family is seeking an experienced, discreet chauffeur to drive an SUV on a fixed weekly schedule that includes regular weekend work. The role includes regular trips to New Haven (Yale), New York City, Long Island, and local airports (JFK, EWR, LGA, etc.), as well as occasional errands. This is not a Monday–Friday role—candidates should expect a genuinely mixed weekly schedule that includes weekend driving on a recurring basis. Candidates must have at least five years of experience as a private chauffeur, not as a limousine or rideshare driver.

COMPENSATION

• Base: $80,000–$100,000/year.

• Overtime paid in accordance with Connecticut labor law for hours beyond the standard schedule.

• Health insurance stipend.

• Vehicle provided and garaged on the property; not available for personal or take-home use.

SCHEDULE — READ CAREFULLY

We're stating this plainly because schedule fit is the single biggest reason placements don't work out: this is not a light-weekend role. The realistic weekly commitment is:

•       Recurring Sunday night OR Monday morning pickup in Manhattan—this is a fixed part of the week, not an occasional request.

•       A minimum of two Saturdays per month, with the likelihood of more depending on the family's calendar.

•       Three to four weekdays per week driving to New Haven (Yale), with the driver either remaining on-site between 9:00 AM and 3:00 PM or returning to Greenwich for local family transportation, errands, and household tasks—provided the driver can return to New Haven for the scheduled pickup. Thursdays may require availability until approximately 6:30 PM.

•       Occasional evening transportation to New York City, Long Island, and other destinations in the greater New York metro area.

•       Additional days as needed for local transfers and occasional errands as requested.

If a candidate needs a role with weekends reliably off, this is not that role. We would rather lose a candidate at this stage than have them accept and leave once the real schedule becomes clear.

FLEXIBLE SCHEDULE REQUIRED

·       Primary reason previous drivers have said no: The recurring weekend obligation—particularly the fixed Sunday-night or Monday-morning Manhattan pickup and the requirement to work at least two Saturdays per month, with the possibility of additional Saturdays.

·       Growing family: The wife is pregnant and due in January, so the driver must be prepared for evolving transportation needs and additional schedule flexibility as the family welcomes the new baby.

·       Adaptable weekday availability: Able to handle three to four weekly trips to New Haven, remain on-site or return to Greenwich between trips, and be available until approximately 6:30 PM on some Thursdays.

·       Evening and short-notice flexibility: Comfortable with occasional evening transportation to New York City, Long Island, airports, and other regional destinations, plus additional local driving as needed.

·       Dependable schedule fit: No recurring personal conflicts that would interfere with weekend, early-morning, evening, or variable-hour assignments.

·       Proactive communication: Able to confirm availability, anticipate timing changes, and communicate promptly when traffic or schedule adjustments arise.

·       Local readiness: Must live within 30 minutes of Greenwich and be able to report reliably for early or changing start times.

RESPONSIBILITIES

•       Provide safe, punctual transportation to and from New Haven, local airports, and other destinations as directed.

•       Plan routes proactively, anticipate traffic, and adjust timing or routes in advance rather than reacting in the moment.

•       Wait on-site during appointments as needed.

•       Maintain the vehicle in pristine condition, including washing, detailing, and checking fluids.

•       Keep mileage and fuel records.

•       Run occasional errands for the family.

•       Garage and store the vehicle on the property at all times; the vehicle may not be taken home.

•       Maintain strict discretion and confidentiality.

•       Communicate proactively about traffic, delays, or schedule changes.

QUALIFICATIONS

•       Must live within 30 minutes of Greenwich, CT.

•       Minimum of five years of experience driving for a private family (not commercial or rideshare driving).

•       Able to commit to a schedule that includes recurring Sunday night or Monday morning pickups and at least two Saturdays per month — please do not apply if weekend availability is uncertain.

•       Quiet, professional demeanor — comfortable with a low-profile, discretion-first role.

•       Impeccable timekeeping; punctuality is non-negotiable.

•       Strong working knowledge of regional traffic patterns and ability to plan ahead accordingly.

•       Clean driving record and valid driver's license; able to pass a background check and drug screening.

•       Comfortable driving a late-model luxury SUV.

•       Familiarity with the I-95/Merritt Parkway corridor and CT airports.