Position Summary/Job Duties: | 6–8 hours/week | $25–$30/hour | Madison Near-West Sid
We're looking for a responsible, outgoing, fun-loving person to become a trusted Family Assistant for our active family with three school-aged kids.
The role will start at approximately 6–8 hours per week, with the majority of the time spent helping manage the kids' sports and activity schedules. We're looking for more than a driver. We'd love to find someone who genuinely enjoys kids, loves sports and being active, and wants to build a relationship with our family.
Our kids are independent, easygoing, funny, active, and very used to busy sports schedules. Previous babysitters will happily confirm that they're pretty darn easy to hang out with.
What You'll Do
- Help transport kids to and from sports practices, activities, and occasional events
- Take ownership of assigned activity logistics, including keeping track of schedules, planning pickup/drop-off times, and helping identify conflicts
- Communicate with coaches or other parents when needed
- Run occasional errands between drop-offs and pickups, such as Costco or Target runs, Amazon/UPS returns, package drop-offs, or prescription pickups
- Occasionally transport more than one child or help coordinate carpools
- Potentially babysit outside regular hours for additional pay
You will not be expected to sit at practices. Once a kid is safely where they need to be, you may be off to transport another kid, tackle an errand, or enjoy some downtime before the next pickup.
Schedule
Approximately 6–8 hours per week, primarily weekday afternoons and evenings between roughly 3:00–8:00 p.m.
The regular weekly schedule will be based on school and sports schedules and should remain fairly consistent week to week. Exact days and hours will be finalized once fall sports schedules are available.
There may occasionally be opportunities for additional hours, including babysitting.
We're looking for someone who can commit for the 2026–27 school year, with the possibility of continuing into summer and becoming a year-round position.
Position can begin immediately for the right person.
Who We're Looking For
The right person is someone our kids will genuinely enjoy spending time with and look up to.
You should be:
- Someone who genuinely loves kids and has previous experience working with or caring for them
- Outgoing, friendly, positive, and comfortable joking around
- Interested in sports, outdoor activities, or an active lifestyle
- Extremely dependable and punctual
- Mature, trustworthy, and comfortable taking responsibility
- A strong communicator who is comfortable interacting with coaches and other parents
- Self-directed and able to figure things out without needing constant instructions
College students are absolutely encouraged to apply. Someone age 20+ is preferred, but we'll happily consider a younger applicant who has the maturity and experience we're looking for.
Driving Requirements
Because transportation is an important part of this position, applicants must have:
- A valid driver's license
- A safe and reliable vehicle
- A good driving record
- Appropriate auto insurance
- Comfort driving children around Madison, generally within about a 25-minute radius
A background check and driving-record check will be required before hiring.
Location
We're located on Madison's near-west side near Hilldale Shopping Center. Because the position involves relatively short shifts and frequent transportation, we're strongly hoping to find someone who lives within approximately 10 minutes of Hilldale, ideally on the near-west side, downtown, or near the UW campus.
Compensation
$25–$30/hour, depending on experience.
About Our Family
We're a busy, active family with three kids: boy/girl twins in 5th grade and an 8th-grade daughter. All three play soccer along with various other sports and activities throughout the year, so there is rarely a shortage of practices, games, gear, or places to be.
The kids are independent, easygoing, funny, and social. They love sports and the outdoors, are comfortable meeting new people, and are genuinely fun to be around (we have past babysitters that have said they are the best kids they’ve ever babysat!). We're hoping to find someone who will get to know them, joke around with them, cheer them on, and become another trusted adult in their lives.
Mom owns a digital marketing company, and Dad works in environmental services for the State of Wisconsin. We're divorced but live near each other and have an excellent co-parenting relationship and a great working partnership when it comes to raising our kids. Depending on schedules, our Family Assistant may occasionally coordinate with either parent, but the majority of the role will be based out of Mom's home near Hilldale.
Our household is casual, active, and fun, and we're hoping to find someone who feels less like "the person who drives us places" and more like an extension of the family. The goal is to find someone we trust, the kids genuinely enjoy, and who wants to take some ownership in helping our busy family life run a little more smoothly.
Where This Could Go
We're hoping to find someone who wants to stick around.
This may start as an 6–8 hour/week position focused primarily on sports transportation and errands, but for the right person, we'd love for the role to grow over time.
As we build trust, there could be opportunities for additional hours, more responsibility, babysitting, and eventually a larger Family Assistant/Household Manager role.
Ultimately, we're looking for someone who can become another trusted person helping us share the responsibility of running a busy household and family.
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