A warm, active family on the Upper West Side is seeking an experienced Nanny/Family Assistant to care for their two boys, ages 5.5 and 6. The boys are six months apart, attend kindergarten together, and have been raised much like twins. The family is looking for a confident, engaging caregiver who genuinely enjoys spending time with children and can keep up with two active boys. 

The ideal candidate will also be comfortable maintaining firm, respectful boundaries, reinforcing manners, and helping the children develop responsibility and independence. The family values a consistent, authoritative approach to childcare and wants someone who can use patience, humor, and good judgment while upholding household expectations.

This is a collaborative position as the family has a long-term weekday nanny and is looking for someone who can complement the existing childcare arrangement. There are also three older children, who visit periodically; primary childcare responsibilities are just for the two younger boys.

The family is open to either a full-time career nanny or a part-time candidate who can provide consistent weekend coverage. For a full-time candidate, responsibilities may expand into light Family Assistant work while the boys are at school. The family values flexibility, initiative, and long-term relationships with their staff.

The family is open to relocation candidates IF they have prior experience working in NYC. 

Schedule: Friday and weekend availability are essential. Full-time options include Wednesday–Sunday or Thursday–Monday, with 50 guaranteed hours. The schedule will either be 12:00 pm to 10:00 pm, likely on weekdays, with weekend shifts likely being 9:00 am to 7:00 pm. The family is also open to a part-time arrangement with approximately 20 guaranteed hours over the weekend, with possibly Friday night coverage as well.

Start Date: ASAP, with flexibility for the right candidate.

Travel: The family spends summers in the Hamptons and travels domestically and internationally throughout the year. Typical trips include winter and spring breaks, with destinations such as Montana and the Bahamas. The family may also travel to the Hamptons on weekends outside the summer season.

For full-time candidates, summer coverage will involve living in during scheduled working days. The nanny will have fully private living accommodations and will never be required to share a bedroom with the children. Overnight childcare is not required when the parents are present.

The family is also open to a part-time candidate who is unable to travel.

• Provide attentive, engaging care for two kindergarten-aged boys

• Plan and participate in developmentally appropriate activities, including sports, outdoor play, games, puzzles, arts and crafts, reading, and educational outings

• Organize playdates, museum visits, shows, and other enriching activities

• Assist with school drop-offs and pickups as needed; the boys' school is approximately a 10-minute walk from home

• Manage the children's daily schedules, activities, and routines

• Reinforce household rules, manners, respectful behavior, and age-appropriate responsibility

• Maintain consistent boundaries while using patience, humor, and effective communication

• Encourage independence and teach the children to participate in cleaning up after themselves

• Prepare simple, nutritious meals and snacks for the children

• Handle children's laundry and maintain their bedrooms, play areas, toys, and belongings

• Manage children's wardrobes, including seasonal organization and identifying items that need to be purchased or replaced

• Pack and unpack for family travel

• Assist with light household tidying and occasional laundry or household tasks as needed

• Support the existing nanny and collaborate with parents to ensure consistent care

• Assist with homework as the boys get older

Additional Family Assistant responsibilities for a full-time candidate MAY include:

• Booking children's activities and organizing tickets and outings

• Assisting with birthday parties, gifts, and thank-you notes

• Grocery shopping, errands, and occasional dry-cleaning pickups

• Helping with household organization, inventory, and restocking

• Assisting with family packing and unpacking

• Taking on other appropriate household support responsibilities based on the candidate's experience, strengths, and available hours

• 5 years minimum of professional childcare experience, particularly with preschool and early elementary-aged children

• Energetic, playful, and genuinely interested in children's development

• Comfortable managing two active children with different personalities and needs

• Confident establishing boundaries and reinforcing manners and household expectations

• Able to remain calm, patient, and consistent during challenging moments

• Strong communication skills and a collaborative approach

• Flexible, adaptable, and comfortable with changes to schedules or family plans

• Organized, proactive, and willing to assist with light household responsibilities

• Comfortable working alongside another nanny and other household staff

• Experience in a Family Assistant role is a plus but not required

• Comfortable supervising children in the water

• A strong swimmer and an interest in sports are highly desirable

• Valid driver's license and clean driving record

• Comfortable driving in the Hamptons; a family vehicle will be provided

• Able to safely swim/supervise children in the water 

• Valid passport and ability to travel internationally for candidates participating in family travel

• Comfortable with domestic and international travel

• Willing to live in during scheduled working shifts in the Hamptons during the summer for a full-time arrangement

• Flexible and comfortable with occasional weekend trips throughout the year

• Strong English communication skills

• Familiarity with navigating New York City

• Legally authorized to work in the United States

• Willingness to rotate holiday coverage with the family's current nanny is preferred but not required. The family is flexible and can accommodate candidates who need specific holidays off

• Compensation: $40–$50/hr,(PT: $41,600-$52,000) (FT: $114,400-$143,000) 

• Overtime: Paid at 1.5 times the regular hourly rate after 40 hours per week.

• Guaranteed Hours: Approximately 20 hours per week for a part-time position or 50 hours per week for a full-time position, depending on the agreed schedule.

• Employment: W-2.

• Paid Time Off: The family offers two options:

• Three weeks of PTO scheduled around the family's travel: one week at Christmas, one week during spring break, and one week during the summer.

• Two weeks of PTO at the nanny's discretion.

• Sick Days: Five paid sick days.

• Holidays: Paid holidays or holiday pay when working.

• Health Insurance: A health insurance stipend is available for full-time employees; amount to be discussed.

• Travel: Additional compensation for travel, with applicable overtime.

• Bonus: Potential annual bonus.

• Transportation: MetroCard or transportation assistance may be provided. Transportation home will be covered when working until 9:30 p.m. or later.