Big Sky, Montana | Organized ROTA Nanny/Family Assistant Wanted For Dynamic, Travel-Rich Family

A vibrant, on-the-go family is seeking a rotational family assistant/nanny to join their team and support their bright, active children and household. This is a dynamic, travel-rich role for someone who thrives in ever-changing environments and is excited to live and work across multiple locations.

‍

• Location: Big Sky, Montana, for approximately one year, with planned relocations
• Ages of children: 4 and 6 years old
• Start date: As soon as they find the right fit!
• Schedule: Full-time rotational schedule, typically 1 week on and 1 week off, Monday to Monday from 7:00 AM to 7:00 PM, with 84 hours per week guaranteed. The family is open to tailoring the rotation, including longer rotations, in collaboration with the nanny team to ensure seamless 24-hour coverage
• Compensation: The family is offering an hourly and overtime rate equivalent to an annualized base compensation of $110-150k/year dependent on candidate experience.
• Benefits: The family will provide benefits including double-time paid holidays for holidays that fall on your rotation, medical, dental, and vision insurance, life insurance, short-term and long-term disability insurance, wellness benefits, a Flex Spending Account (FSA), and Dependent Care FSA, and 401(k). The family also offers a 5:1 charitable matching program and $3,000 (plus T&E) professional training benefit for approved job-related training conferences and certifications relevant to the candidate’s career goals.
• Live-in/Live-out: Live-in while on-duty, live-out while off-duty. A private apartment on-site or nearby will be provided. When one parent is traveling, the nanny will stay in the family’s home (private quarters).
• Fly-in/Fly-out: The family is open to fly-in / fly-out candidates within the continental US.

‍

Household dynamic:

• The family is warm, close-knit, and fun — they ski, surf, travel often, love the outdoors, and approach family life with a sense of adventure that carries into everything they do. They value kindness, reliability, good judgment, clear communication, and a home that feels calm, joyful, and well-cared-for.They are currently transitioning to Big Sky, Montana, where they plan to spend approximately one year. Longer term, they intend to live between Malibu, Europe, and Chicago, embracing a travel-rich lifestyle while their children are young, before eventually settling back in Chicago. Their 6-year-old daughter is social, curious, and loves spending time with friends. She enjoys swimming, building with Legos, and reading, and will be entering an IB elementary program. Their 4-year-old son is energetic and playful, with a love for riding his bike, playing with cars and trains, and exploring the outdoors. He is also an imaginative storyteller who loves creative play.
• Both parents have demanding and frequently changing schedules, with regular travel that may require the nanny to take full charge for several days at a time. They are highly involved in their children’s lives and take an intentional, collaborative approach to parenting. They engage in weekly and annual family meetings, align on shared values and boundaries, and use tools like Asana to track goals and responsibilities across the household. The family also employs an estate manager, two executive assistants, and a large family office, creating a collaborative and well-supported environment. The family office also offers events, learning opportunities, and security training.

‍

Ideal candidate:

• This is a family assistant first role. With both children in school full-time, the right person will provide excellent care before and after school, then turn their attention to the household during school hours. During summer break, the job will shift to a more childcare-focused role. The family wants someone who is comfortable owning the home during those off-peak hours and doesn't need to be directed to find meaningful work. Cooking, driving, laundry, errands, household organization, vendor coordination, and proactive restocking are all fair game.
• This role is ideal for a warm, engaging, and highly organized candidate who is confident managing a household with many moving parts and thrives in a dynamic, multi-location environment. A naturally playful, creative person who can connect with children through imaginative, child-led experiences while maintaining structure and consistency in daily routines will fit in. The family values a balance of structure and flexibility, maintaining consistent routines while adapting to travel, new environments, and evolving needs. A confident, capable professional who can take full charge during parental travel and seamlessly manage the day-to-day needs of the household will be an excellent fit. The family values a tech-savvy candidate who is comfortable using tools such as Slack, email, and Asana to communicate, track responsibilities, and stay aligned, including sharing regular updates and photos with the family.
• Experience living or working in snowy or mountainous environments, particularly in close-knit communities such as Big Sky, Aspen, Breckenridge, or Jackson Hole, is highly valued. Confidence driving in snow and mountainous terrain is important, and the family is open to supporting a candidate in taking a driving course in Montana. 
• Weekly hand-off meetings are an important part of the role, so clear communication and organizational skills are essential. Experience traveling with families, managing packing and logistics, and staying organized on the road is a must. The family values clear communication and accountability, with performance goals tracked on a quarterly basis and bonus opportunities tied to goal achievement.
• Responsibilities include, but are not limited to: 
  
  • Childcare and Family Support
    
    • Provide warm, safe, attentive, and engaging care for two children, ages 6 and 4
    • Help the children get ready for school, activities, travel, meals, and bedtime routines
    • Drive the kids to and from the bus stop, to activities, and to run errands.
    • Create a positive, age-appropriate environment for play, learning, and daily life
    • Support school-day transitions, after-school routines, activity logistics, and full coverage when parents are traveling
    • Maintain strong communication with parents and their team about schedules, needs, supplies, and any concerns
    • Reinforce routines, manners, and age-appropriate independence as the children grow
  • Household Management and Daily Operations
    
    • Own the home during school hours: laundry, light housekeeping, some laundry, tidying, organizing, errands, and supply management
    • Plan and prepare family meals, including breakfast, school lunches, dinner, and snacks
    • Manage grocery shopping and household restocking proactively, before things run out
    • Maintain a calm, clean, and well-run home environment
    • Take initiative during any downtime by identifying and completing household tasks without being asked
  • Family Schedule and Logistics
    
    • Maintain and update the family calendar in real time, including school, activities, appointments, travel, and vendor visits
    • Coordinate transportation, reservations, activity logistics, and packing for family travel and day-to-day needs
    • Anticipate upcoming needs and surface conflicts before they become urgent
    • Communicate schedule updates clearly to parents, estate managers, vendors, and co-nanny
  • Estate and Vendor Support
    
    • Work closely with the family's estate managers to maintain the Big Sky home at a high standard
    • Coordinate vendor visits: scheduling, access, completion confirmation, and status updates
    • Support household projects during school hours, including organizing, inventory, seasonal prep, and guest readiness
    • Help maintain family vehicles: clean, fueled, stocked, and ready
    • Maintain discretion, privacy, and sound judgment when working inside the home and with family information
    • Collaborate with the co-nanny during weekly handoff meetings to ensure seamless coverage and clear communication

‍

Qualifications:

• Prior experience as a nanny for a private family, ideally with children in a similar age range
• Family Assisting experience 
• Longevity of 2+ years in at least one previous role
• Prior ROTA experience
• Valid driver's license, clean driving record, and confidence driving children in changing weather conditions
• Valid passport (or be able to obtain one)
• Confident swimmer
• Comfort with household operations: cooking, laundry, light housekeeping, grocery management, vendor coordination, and errands
• Comfortable preparing light family meals
• Flexible and enthusiastic about frequent, extended travel
• Ability to live in while on duty and live out while off duty
• Partners, family members, and/or pets cannot be housed in any temporary or long-term accommodations provided by the family

‍

This position is open to all Adventure Nannies candidates who are legally able to work in the US. Out of respect for the privacy of the families we work with, we cannot provide any additional information about this position other than what has already been provided in the job description. If you are interested in learning more about the position, please apply!