A warm and high-profile family in Waccabuc, New York, is seeking a highly capable, proactive nanny/family assistant to provide full-spectrum childcare support and manage all child-related household needs for their two young children. This role requires a polished career professional who is calm, deeply organized, and entirely at ease working in a busy household with a medically complex child. The right candidate thrives in a dynamic environment, anticipates the family’s needs without being directed, and brings genuine warmth and steady confidence to everything they do. This is a nationwide search, and a relocation stipend is offered for qualified out-of-area candidates.

The schedule is Monday through Friday, 7:30am to 7:30pm, for approximately 60 hours per week, with occasional Saturday coverage of approximately 5 to 6 hours. The family is open to flexible scheduling arrangements, including a Tuesday through Saturday shift or a modified schedule where Saturday coverage is exchanged for Friday off. Please note that the children are in school for 6 to 7 hours Monday through Friday, during which a 2-hour break will be provided. Flexibility is appreciated for travel, extended hours, and schedule adjustments as needed.

Living arrangements are flexible. The family will consider both live-out candidates and those who prefer to live in during the work week only. A private apartment is available on the property, and this arrangement may be particularly appealing to candidates relocating from New York City. The family will coordinate school transportation collaboratively, as the children’s schedules overlap. The candidate would handle driving for one child while the parent manages the other’s transportation.

It is also worth noting that the mother is home during the day, so this candidate will be working alongside a present and engaged parent. The ideal candidate is comfortable in a collaborative household dynamic and brings the same level of professionalism and initiative regardless of who is in the home.​​​​​​​​​​​​​​​​

• Provide attentive, nurturing, and developmentally appropriate care for both children
• Offer full physical support for the eldest child, who has cerebral palsy, including carrying and transfers to and from the car, up and down stairs, and throughout the community
• Coordinate medical appointments, therapy scheduling, and ongoing communication with the care team
• Encourage the eldest child’s physical development through active play and movement, ensuring she is never sidelined from participation
• Provide the younger child with dedicated outdoor activity, physical play, and close supervision
• Manage the differing activity needs and interests of both children simultaneously with patience and creativity
• Confidently take both children out together independently on a daily basis; this is non-negotiable
• School drop-off and pickup by car, including travel to a specialized school, approximately 30 to 45 minutes away
• Manage and coordinate playdates, classes, and extracurricular activities for both children
• Full meal planning, weekday dinner preparation, and cooking for the family
• Lunch preparation for the children
• Grocery shopping and household supply management
• Closet and clothing inventory management for both children, including identifying outgrown items and coordinating or purchasing replacements
• Organization and tidying of child-related spaces, bedrooms, and play areas
• Light housekeeping of family spaces, including kitchen tidying after meals, children’s laundry, and keeping common areas presentable
• Coordination with the separate housekeeping team for deep cleaning
• Family calendar management and day-to-day household logistics and scheduling support
• Packing and travel preparation for the family
• Occasional errands as needed
• Travel with the family domestically and provide full support while away

• Norland College, MPW, or a minimum of 5 years of experience in a comparable principal-family role is strongly preferred
• Demonstrated experience working with children with special needs; experience with cerebral palsy strongly preferred
• Background in nursing, physical therapy, occupational therapy, or speech therapy a significant plus
• Physical fitness and stamina are non-negotiable; this role involves a high level of physical demand throughout the day, including carrying and transferring a child of approximately 25 pounds repeatedly across various settings
• Highly proactive, organized, and detail-oriented
• Calm, confident, and grounded demeanor; the household calls for steady, optimistic warmth rather than loud or excitable energy
• Flexible, adaptable, and able to anticipate the needs of the family and children without waiting to be directed
• Strong communication skills and professionalism at all times
• Valid driver’s license with a clean driving record; comfortable driving (share responsibility with the Mother) in the New York and Connecticut region
• Current CPR and First Aid certification
• Valid US passport not expiring within the next 6 months
• Ability to travel domestically and occasionally internationally without restriction
• Authorized to work in the United States
• 3 verifiable professional references from comparable principal families required
• Comfortable working alongside a separate housekeeping team in a private household

• $100,000 and above annually, commensurate with experience, paid on the books with overtime built in per New York State domestic worker law
• For live-out candidates: housing assistance is included; a provided rental apartment near the family’s home
• Monthly healthcare stipend
• Paid time off and paid holidays
• Year-end bonus based on performance
• Relocation stipend available for qualified out-of-area candidates