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

A vibrant, on-the-go family is seeking a highly organized, education-focused rotational nanny to join their team and support their bright, active children. 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.

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• 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 $110-130k/year dependent on candidate experience.
• Benefits: The family is open to providing benefits, including paid holidays, 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. Accommodations are provided at each of the family's homes.
• Fly-in/Fly-out: The family is open to fly-in / fly-out candidates within the continental US.

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Household dynamic:

• This warm, adventurous family leads a highly dynamic, multi-location lifestyle. 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 includes a rockstar Adventure Nanny who has been with them for over 4 years, as well as a full-time housekeeper, estate manager, educational consultant, and a large family office that creates a collaborative and well-supported environment. The family office also offers events, learning opportunities, and security training.

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Ideal candidate:

• This role is ideal for a warm, engaging, and highly organized rotational nanny who is confident managing a household with many moving parts and thrives in a dynamic, multi-location environment. The ideal candidate brings a strong educational background, ideally with a focus on early childhood or elementary education, and is passionate about fostering a love of learning through thoughtful, developmentally appropriate engagement. A naturally playful, creative, and able to 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.
• The family seeks someone who can:
  
  • Confidently support early academic skills through structured activities and everyday experiences
  • Adapt lesson materials for travel and create engaging, educational moments outside the classroom
  • Track developmental and academic milestones, providing regular updates to parents
  • Build a warm, trusting relationship with both children while balancing learning with play and outdoor exploration
  • Engage in imaginative, child-led play and support creative expression, particularly for a child who enjoys storytelling and pretend play
  • Work seamlessly as part of a team, especially in coordination with the housekeeper, to ensure daily routines, schedules, and household tasks are aligned
  • Draw on accredited elementary teaching experience to help their daughter keep pace with her program while traveling
  • Prepare healthy, simple meals for the family
• 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.
• Responsibilities include:
  
  • Supporting early academic development through a blend of structured and play-based learning
  • Providing supplemental academic support for the family’s eldest child as she progresses through an IB curriculum, including during travel periods
  • Potentially supporting a homeschool-style learning environment for the youngest child during the family’s time in Big Sky, including planning and implementing age-appropriate, play-based educational activities if the family opts out of a traditional pre-K setting
  • Encouraging creativity and imaginative play, including storytelling, open-ended play, and creative expression
  • Tracking developmental and academic progress and communicating regular updates to parents
  • Maintaining consistent daily rhythms and expectations across homes and environments
    
  • Managing packing, travel logistics, and staying highly organized on the road
  • Preparing daily family meals, including breakfast, school lunches, and dinner
  • Collaborating closely with the existing nanny and household staff to ensure seamless coverage and communication
  • Maintaining flexibility with scheduling in collaboration with the co-nanny and family as locations and travel evolve.
• The family values clear communication and accountability, with performance goals tracked on a quarterly basis and bonus opportunities tied to goal achievement.

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Qualifications:

• Minimum 5 years of full-time childcare or teaching experience
• Accredited elementary or Montessori teaching experience strongly preferred
• Knowledge of developmental milestones and early literacy
• Valid driver’s license and confidence driving in snow and mountain terrain
• Valid passport
• Confident swimmer
• 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
• Spanish or Polish language skills are a plus
• Partners, family members, and/or pets cannot be housed in any temporary or long-term accommodations provided by the family

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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!