A year-round, full-time opening for a Caretaker to manage a New England waterfront estate.

The Property

The property is in New England on the ocean. It consists of 30 acres with 4 acres of highly maintained area. Access to the Property is a three-mile, well maintained dirt road that services a number of other homes, most of which are used only seasonally. The Property’s structures and plantings are subject to harsh seaside conditions and must be maintained according to local regulations restricting run-off to sensitive ponds and shore areas.

The improvements, created in 1999, include a six-bedroom main residence, pool and pool house/exercise room, two-bedroom cottage and equipment shed (“the barn”). The style of all structures is contemporary with extensive decking and expanses of glass. There are two fenced garden areas providing vegetables, flowers, culinary herbs and berries for the Owner.

The Property is used by the Owner for private retreats, primarily in summer, and occasionally by the family’s grown children. The Property must be constantly maintained so that the Owner can visit on very short notice. This will require that all systems, facilities, and grounds be kept in a state of reasonable readiness so that only final touches need be applied prior to the Owner’s arrival.

The Owner

The Owner travels regularly, domestically, and internationally, and maintains a demanding schedule of service on numerous boards. The Owner, while self-described as a “perfectionist” and a “demanding” employer, enjoys many long-term relationships with household, garden and office employees. The staff for this Property should not expect to have a lot of personal contact with the Owner, either on the phone or during visits; most communication will go through the Owner’s office staff.

The Position

This is a full time, year-round position. The Caretaker will be the employee of and will report to the Owner. The workload is affected by season and the Owner’s visiting schedule. The Caretaker may work long hours, seven days a week while the Owner is in residence and somewhat less intensively in winter or when the residence is unoccupied. However, the Owner expects that the Caretaker’s work schedule will include regular, full-time hours Monday through Friday all year except at peak periods when the hours will be extended.

Responsibilities

A detailed list of ongoing chores and special preparations for Owner visits is available. General responsibilities include:

The Caretaker will maintain all structures and outdoor surfaces and the pool and spa and will keep all building systems, vehicles, and equipment (interior and exterior) in top working condition. This position does not involve cleaning per se (see below) but does include assisting in certain projects like window washing as often as necessary to provide spotless glass surfaces throughout the residence and pool house whenever the Property is occupied.

The Caretaker will process all vendor invoices and submit them for payment twice a month. The Caretaker will purchase supplies and equipment as approved by the Owner. The Owner expects a weekly written report including photos as appropriate, via email to the office, covering activities, plans, questions and/or issues for the Owner’s information or decision. The Owner will respond in a timely manner, generally through the office staff.

The Caretaker will occasionally provide local transportation for the Owner and guests, arrange, pickup and return rental cars, when necessary, collect mail daily from a box at the entrance to the dirt road, obtain daily newspapers when the Property is occupied and handle other errands. The Caretaker will supply and maintain the fireplaces.

Other Relationships and Resources

The Caretaker will schedule and oversee contractors and subcontractors and will identify additional contractors and specialists as necessary for ongoing and future projects.

A principal Housekeeper often accompanies the Owner on visits to this Property. The Owner also employs a local Housekeeper who maintains the interiors of the residence, assists in intensive preparation before family visits and assists in daily maintenance of the residence and pool house when the Owner is in residence. The Caretaker must work effectively with the Housekeepers and will engage and supervise additional specialty cleaning or maintenance personnel as necessary.

. It is expected that the Caretaker will be capable of light carpentry and other maintenance tasks and will rely on outside contractors only for more extensive or specialized projects. When required, the Caretaker will schedule and oversee the work of specialized contractors.

. The Caretaker will serve as the Owner’s representative to the local trade community. They will develop and maintain good working relationships with all service providers, schedule and oversee their work and approve/process their invoices for payment.

A private chef accompanies the Owner on visits to the Property when appropriate. The Owner entertains extensively during these visits and engages local kitchen and wait staff as required. The Caretaker is not responsible for any food services beyond stocking the house with basic supplies before the Owner’s arrival and errands during visits.

The Owner is supported by a family office that handles bookkeeping, finance, legal, tax and other matters. The Caretaker will work effectively with this staff to process invoices and otherwise manage local financial matters for the property.

Required Qualifications

• Competence in pool and spa maintenance.
• Proven problem-solving skills, creativity, and the ability to involve others successfully in finding workable solutions.
• Strong work ethic and a willingness to undertake any necessary task.
• Demonstrated ability to provide exemplary service to the Owner, family, and guests in a private estate setting.
• Attention to minute detail and exceptionally high personal and professional standards.
• Excellent personal and professional organizational, prioritizing and implementation skills.
• Strong interpersonal and management skills adequate to maintaining effective working relationships with the Owner, family, staff and a wide variety of vendors and service personnel.
• The sensitivity to always respect the Owner’s preferences and possessions and privacy while in residence.
• Sufficient computer and office skills to maintain basic Property accounts and facilitate communication.
• Excellent communications skills, both oral and written.
• Enjoyment of vigorous outdoor work in all seasons.
• A drive to find pleasure and pride in creating both a beautiful environment and a smoothly running property so as to eliminate stress for the Owner.
• Stamina, positive attitude, and a sense of humor.
• The ability to thrive in an isolated setting and to work effectively and cooperatively as a team member.

Preferred Qualifications

• Ability to perform basic carpentry, electrical, plumbing and machinery repairs.

Compensation

This position offers a competitive full-time salary for the Caretaker. Potential housing on property.

Job Type: Full-time

Pay: $100,000.00 - $200,000.00 per year

Benefits:

• Paid time off
• Relocation assistance

Experience level:

• 5 years

Schedule:

• Every weekend
• Monday to Friday
• On call

Ability to Relocate:

• Edgartown, MA 02539: Relocate before starting work (Required)

Work Location: In person