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Tailor Made Nannies

Nanny + Family Assistant: Madison, WI


Meet the Family


A warm, active, and welcoming Madison family is seeking a dependable, nurturing, and organized Nanny/Family Assistant to become a valued part of their household! With two young boys and busy professional schedules, they are looking for someone who can provide loving, consistent care while helping their home run smoothly.


Both parents work in medicine and value patience, empathy, inclusivity, and open communication. They believe in helping their children understand and navigate emotions, encouraging independence, and approaching everyday challenges as opportunities for learning and growth.


As a family, they love spending time outdoors, staying active, reading, and exploring their community. They're excited to welcome someone who shares their values and hopes to build a meaningful, long-term relationship with their family.


Meet the Children


Boy | 4 Years Old

An active, curious, and wonderfully helpful four-year-old who loves being involved in whatever is happening around him! He has a big imagination and a particular love for Thomas the Tank Engine, BRIO trains, construction vehicles, and digging in the dirt. He's also an enthusiastic reader who loves trips to the library, spending time outdoors, and helping with everyday activities.

He's continuing to develop his independence and emotional regulation skills, and his parents value patient, encouraging guidance, positive reinforcement, and gentle reminders as he continues developing his toileting independence.


Boy | 9 Months Old

A busy, curious little guy who absolutely adores his big brother! He's constantly on the move, crawling, pulling himself up, and practicing walking with his walker. He loves exploring his surroundings and being part of the action.


Both boys attend a Spanish-immersion daycare full-time, and the family hopes to find someone who will complement their routines, encourage their interests, and provide a consistent, loving presence in their lives.


Schedule 


30 guaranteed hours per week


The family is seeking someone who enjoys a combination of childcare and household support, with flexibility to accommodate their busy hospital schedules.

  • Sunday: Approximately 3–4 hours beginning around 12:00–1:00 PM, primarily focused on engaging activities and outings with the boys so Mom and Dad can plan for the week ahead. 
  • Monday or Tuesday: One day off, with the other  involving daycare pickup and evening support from approximately 4:00–7:00 PM. The schedule will be determined in advance.
  • Wednesday: Approximately 8 hours dedicated primarily to grocery shopping, meal preparation, cooking, and household responsibilities.
  • Thursday: Approximately 10:00 AM–6:00 PM, with household support and childcare as needed.
  • Friday: Approximately 10:00 AM–6:00 PM, with household support and childcare as needed.

Flexibility is important, particularly when the boys are home due to illness, daycare closures,  or other scheduling needs. The family will communicate adjustments as far in advance as possible and guarantees 30 hours of pay each week.


Childcare Responsibilities

  • Providing loving, attentive, and developmentally appropriate care for both boys.
  • Assisting with daycare pickups, meals, and evening routines.
  • Planning engaging activities and outings that encourage creativity, curiosity, and learning.
  • Prioritizing outdoor play and physical activity year-round.
  • Supporting emotional development through patience, empathy, and positive guidance.
  • Encouraging age-appropriate independence, toileting skills, and participation in household cleanup.
  • Providing attentive infant care, including feeding bottles and supporting developmental milestones.
  • Assisting with transportation to activities and extracurriculars as needed.

The family values a caregiver who is genuinely engaged with the children, whether that means building train tracks, exploring outdoors, visiting the zoo, or spending an afternoon reading together.


Family Assistant & Household Responsibilities


A significant portion of this position will focus on household support while the boys attend daycare, with a particular emphasis on cooking, meal preparation, and organization.


Meal Planning & Cooking

  • Planning and preparing nutritious family meals, snacks, and child-friendly options.
  • Researching new recipes for the parents to review and select.
  • Grocery shopping and maintaining necessary household food supplies.
  • Preparing meals in advance to simplify busy evenings.
  • Introducing variety into the family's meals and encouraging the children to try new foods.
  • Maintaining a clean and organized kitchen following meal preparation.

The family enjoys healthy, balanced meals, including chicken, salmon, vegetables, and other wholesome ingredients. They do not eat red meat but are open to trying new foods. Gourmet cooking isn't expected; they simply hope to find someone who genuinely enjoys cooking and can bring creativity and variety to their weekly meals.


Household Organization & Support

  • Managing family laundry and changing bed linens weekly.
  • Running errands and purchasing household supplies.
  • Organizing closets, pantry spaces, and children's areas, including purchasing organizational supplies as needed.
  • Seasonally rotating children's clothing, toys, and books.
  • Maintaining a functional, organized playroom and encouraging the boys to help with cleanup.
  • Assisting with larger household organization projects as time allows.

The family would love someone who takes initiative, anticipates needs, and enjoys creating systems that make everyday life easier.


Ideal Candidate

Above all, the family is seeking someone who is exceptionally reliable, calm, patient, and empathetic. They want to feel confident that their caregiver can navigate the natural ups and downs of caring for young children with a steady, understanding approach.


Their ideal candidate will:

  • Have experience caring for infants and preschool-aged children.
  • Embrace positive, respectful caregiving that prioritizes emotional development and understanding.
  • Genuinely enjoy cooking, meal planning, and supporting a busy household.
  • Be organized, proactive, and comfortable working independently.
  • Love being active, spending time outdoors, and planning engaging experiences for children.
  • Be flexible, adaptable, and comfortable balancing childcare with household responsibilities.
  • Share the family's values of kindness, inclusivity, and respect for others.
  • Be seeking a long-term position and meaningful relationship with the family.

Bonus: Spanish-speaking candidates are especially welcome, as both boys attend a Spanish-immersion daycare.


Compensation & Benefits

  • Hourly Rate: $30–$35/hour, depending on experience and qualifications.
  • Guaranteed Pay: 30 hours per week.
  • Overtime: Time and a half for hours worked beyond 40 per week.
  • PTO: 5 days annually of the nanny's choosing
  • Additional PTO: Up to two additional weeks annually when the family is traveling or care is not needed, coordinated with the family's schedule. Household projects may occasionally be available during these periods.
  • Sick Leave: 3 paid sick days annually.
  • Paid Holidays: Federal holidays falling on regularly scheduled workdays
  • Health Insurance: Negotiable stipend based on the nanny's needs.
  • Transportation: Personal or family vehicle for work-related driving, with mileage reimbursement when using a personal vehicle.
  • Vaccinations: Seasonal flu and COVID vaccinations requested.
  • Start Date: Week of December 28, 2026, with a possible overlap period for a smooth transition.


This is a lovely opportunity for an experienced Nanny/Family Assistant who enjoys the balance of nurturing young children and helping a busy household thrive.


The family is looking for much more than someone to complete a list of tasks. They hope to find a trusted, long-term partner who will develop meaningful relationships with their boys, bring calm and consistency to their days, and take pride in helping their household run smoothly.


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Celebrating 11 beautiful years!

September marks 11 years of Tailor Made Nannies.


We are incredibly honored to have supported and partnered with so many wonderful families and nannies over the years.


Thank you for trusting us to do what we love most.


Here’s to the many years ahead!