Meet a Mom: Meet Sarah Davis, Founder of Olive Us App! | Chicago North Shore Moms

Hello friendly faces! It’s that time of the week! We’re back with a new CNSM Meet a Mom spotlight brought to you in part by Mary Gifford of Gifford Law. We are excited to introduce you to former Chicago mom of three not-so-little-anymore kids, founder of Olive You Nanny and now founder of Olive Us App, a nanny placement app for busy parents, Sarah Davis!

Sarah Davis is an entrepreneur, female founder and a woman with true grit. She had all three of her kids in her 20’s founded a company, Olive.You.Nanny, and most recently developed a ground-breaking babysitting app to help match families to sitters who truly love what they do. What’s more, Sarah is paving the way for young female entrepreneurs to take babysitting to a whole new level of empowerment and small business skills. Get to know Sarah’s journey as a female founder and more importantly, how you can start scooping up those babysitters! Welcome, Sarah!

Hi Sarah! Please introduce yourself. Where are you from originally? When and where did you live in Chicago?

Hi! I’m Sarah, and I’m originally from Door County, Wisconsin. I’ve lived in many places, including MN, CA, CO, IL, and now TX! I currently live in Austin, TX. I lived in Chicago for about 10 years and I’ve lived in places all over the city but ended up in Ukrainian Village.


You’re a mom! How many kiddos do you have, and how old are they? Feel free to brag here.

Brag? Never. I have 3 kiddos and they’re all enrolled in a junior NASA development program (top secret). Kidding! :-). Not so little, Davis is 16, Maeve is 15, and Remy is 12 (almost 13). I had all 3 of my kids in Chicago. Davis was born at the old Prentice….WOW, what an upgrade for the other two kids being born at the new Prentice! Having three little ones in the city was awesome. I loved that I could throw them in the stroller and get anywhere either walking or on the L train. When Davis turned 6, we decided to move to Austin. I have to say….I miss Chicago a ton and can see myself moving back when the kids are in college. Anyone know a good realtor who specializes in lofts?



What are one or two things people would be surprised (or fun facts) to know about you?

I started my first company when I was 24. (I think the naivety of being so young played to my advantage.)

I had all 3 kids in my 20’s.

I broke my ankle when I was 40 trying to be young and cool playing on a club soccer team. For the record, I was young, and cool. Still am!


What gets you through a tough day?

Ha! My nights. Seriously, I love chilling with a glass of wine. I have a very supportive partner whom I rely on a lot to get me through my tough days. I think his support is golden. My kids are also entertaining and at a great age to give me pep talks. I feel like we are all one unit and support each other during our tough days. It’s amazing what incredible advice teenagers can give.


What is your mantra?

I focus on two, actually. “No risk, no reward” and “If it was easy, everyone would do it.” Also, I often tell myself: “Things are looking up.”


Congratulations on your successful nanny placement agency, Olive.You.Nanny! Even more congratulations are in order for your new startup, Olive Us App. For those of us not familiar, please tell us about Olive You Nanny Agency.

Olive You Nanny is my first company. I started OYN in 2004. We are almost 20 years old!! We are a nanny placement agency that specializes in personal relationships and making sure both families and nannies have a perfect match. I was a nanny before starting the company. I really felt that this space needed an agency that valued getting to know each family personally and then found candidates that would become a part of their family. I live and breathe the nanny world:)


We’d love to learn more about the Olive Us App! What is it?

YAY! I’m so very excited to have just launched Olive Us! This has been a 5-year long project. In the last five years, there have been many changes; personally, I got divorced in 2020, COVID, and my development team in Ukraine was displaced by the Russian invasion…. it’s been a long few years! But, we have worked SO very hard on this project, and I’m really proud of it.

Olive Us is a babysitting app where you match, book, and pay sitters all on one platform. You can request as many sitters as you’d like and then accept the best match for your family. Think: Bumble meets Uber, meets It’s an on- demand platform for busy parents. This is the MVP, we have much more in store for Olive Us!



How does the Olive Us app differ from all of the other apps out there? What need are you filling that parents needing childcare didn’t have filled before?

At the core of Olive Us is a proprietary matching algorithm that was developed by me, based off of my decades of experience in this industry. This has never existed on a babysitting app. I have taken what I have learned with running a nanny agency and created an algorithm that matches personalities (parents and sitters) to optimize sitter hiring. For example, is your family artsy, do you love to hike, goes to concerts, are you creative and fun? Or is your family more chill, love to read, play board games and watch movies? Of course, there can be a mix, but this algorithm matches you with sitters who align with your family’s dynamic.

Olive Us is also targeted to college students and nannies. It’s not so much a “neighborhood sitter” but a more experienced sitter. I’m very passionate about advocating for women entrepreneurs, and the Olive Us platform was built to empower women to treat and run their sitting business as a real business, because it is. For example, I have now spoken at a number of local (Austin and Chicago) sorority chapter meetings, and empowering these women to take control of their financial freedom at a young age is so important to me.



How long did it take to create the app from start to finish? Tell us about the process a bit.

Five years. Actually 5 1/2 years. When development began, I had been running Olive.You.Nanny Agency for 15 years and really wanted to scale the business. I ran through several scenarios, and it kept coming back to parents needing last-minute help and on-demand help. At that time, there weren’t any babysitting apps. (I’m thankful that now there are a few and that parents and sitters have embraced the idea!) I wanted to use my expertise to create a platform that was unique and that actually matched you with sitters that are like-minded and similar in personality to your family. It’s incredibly challenging to know how to do this unless you have been matching families and nannies for so many years.

There are a lot of unsaid things to pick up on when I meet a family. I took my knowledge of matchmaking and created this algorithm to make the process simple and more precise. You can actually match, book, and pay sitters in a few clicks. Olive Us also allows you to video chat with your sitter beforehand. This is important for families to know who’s coming over to take care of their kiddos, and great for sitters to know a little more about the families too. Call it: 2-way screening. 🙂


What was the scariest thing about starting over with your business?

I think the hardest thing now about starting a new business (still run Olive.You.Nanny) is having three kids and making sure I have enough time for everyone and everything! It takes a ton time and money to start a new business. It’s a balance, for sure.


What are you most proud of with your entrepreneurship throughout the years?

It’s been 20 years, so I could go on forever here! I started Olive.You.Nanny to bridge the the between families and nannies. It’s important to me that the match takes priority over everything else. When that connection is made, everything else falls into place. I have found it extremely rewarding to know how many women we have helped, not only to find their long-term families, but also to help in their employment journey. We have helped thousands of women find a job; that’s really cool to think about.

Olive Us was built to achieve the same goals, but this time, targeting young women who are just getting started in making their own income. We want to empower young women to treat their babysitting business like a real business. It’s a great place to get started in creating their independence.


What should our members do to start using this app? 

Here is the link to download Olive Us in the Apple Store! Make sure to complete your family profile so you can start booking sitters. A 30 second “family intro” video in your profile never hurts to “market” your family to sitters. Olive Us is intended to be a two- way marketplace for families and sitters. Don’t skimp on your family profile! Having your current sitters make a profile is also a great idea. This way, you can book and pay them on the platform for an easy, all-in-one process.

And we LOVE feedback; let us know what you think! The first 30 days are free when you sign up!

You can also follow us on Instagram for tips and tricks of the app.

About our Meet of Mom Sponsor

A very heartfelt thank you to CNSMoms’ Meet a Mom sponsor, Lake Forest mom of three and owner of Gifford Law, a solo Estate Planning Firm (wills and trusts). Mary, we appreciate your support of local moms in our North Shore communities! Learn more about Mary by visiting her Meet a Mom spotlight here! Contact Mary directly here: [email protected].

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