WORKING WITH OLIVE YOU NANNY MILWAUKEE
Looking for your next dream nanny job? At Olive You Nanny, we do more than just place nannies—we match you with families who truly value your expertise. We take the time to understand your experience, preferences, and career goals to ensure the perfect fit. Our families are carefully screened, and we advocate for competitive pay, benefits, and respectful working conditions. From introductions and interviews to contract negotiations, we handle the details so you can focus on what you do best. Plus, with our ongoing support and nanny community, you're never alone in your journey. Let us help you find a role where you feel appreciated, supported, and excited to go to work every day!
Join Our Sitter Club – Flexible Jobs with Trusted Families!
Are you an experienced and reliable sitter looking for flexible, well-paying jobs with wonderful families? We’re excited to introduce our Sitter Club booking system with Book Lilli—making it easier than ever for you to get matched with families who need occasional care!
At Olive You Nanny Milwaukee, we’ve spent over a decade building a trusted reputation for placing exceptional nannies. Now, we’re bringing that same high standard to our sitter network. Every family you’ll work with has been connected through us, ensuring safe, professional, and respectful working environments.
Why Join Our Sitter Club?
✔ Flexibility on Your Terms – Pick up babysitting jobs that fit your schedule.
✔ Vetted, Trustworthy Families – We connect you with great families in the community.
✔ Easy Booking with Book Lilli – No more back-and-forth emails—just accept jobs through our simple text based system!
✔ Competitive Pay – Earn great rates for your experience and professionalism–family pays you directly!
PLEASE REVIEW OUR NANNY REQUIREMENTS BELOW.
When you are ready to apply, click “Apply Now.” Once we have reviewed your application, a placement specialist will be in touch if an interview is desired. We look forward to the possibility of working with you to place you with the perfect family.
In order to be considered for a nanny position with Olive You Nanny Milwaukee, you must meet the minimum requirements listed :
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Have at least 3 years experience as a nanny or childcare provider
Be CPR + First Aid Certified
Pass a background check, including having a clean driving record
Consent to a Social Media Screening
Provide at least 3 childcare references
Provide verification of meeting US employment requirements
Minimum Education : GED
Participate in face-to-face interview with Olive You Nanny

APPLY NOW TO JOIN OUR TEAM
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APPLY NOW TO JOIN OUR TEAM |

Supporting Your Journey to the Perfect Family match
As a nanny, the search for a family to work with can be daunting. Olive You Nanny offers a streamlined process to ensure each nanny is successfully matched with a vetted family and has ongoing professional support.
01. VETTED FAMILIES:
Olive You Nanny screens families thoroughly, which ensures the nanny knows the family is serious, safe, and prepared to invest in quality care.
02. EFFICIENT JOB MATCHES:
We get to know each nanny's unique skills, values, and needs, which means we can match nannies with families that align with their specific strengths, preferences, and schedules.
03. PROFESSIONAL SUPPORT:
Olive You Nanny provides contract guidance, helps set clear expectations, and supports both the nanny and family through negotiations, which can take the pressure off the nanny.
04. ONGOING ADVOCACY:
Olive You Nanny remains involved even after placement, offering resources, advice, and support to help nannies address any challenges that come up.
05. STREAMLINED PROCESS:
Olive You Nanny handles background checks, interviews, and contract creation, so nannies can focus on connecting with the right families.
OLIVE YOU NANNY NOT ONLY MATCHES NANNIES WITH GREAT FAMILIES IN THE MILWAUKEE AREA BUT ALSO PROVIDES A STRONG SUPPORT SYSTEM THROUGH THE ENTIRE PROCESS.