Introducing to the Chicago North Shore Moms community Sarah Davis, an unwaveringly devoted mom of three and the founder of Olive You Nanny, a trusted nanny placement agency celebrating 20 years of supporting families.
Splitting her time between Chicago and Austin, Sarah has become a master of balance. Raising three teens, running a thriving business, and pursuing passions that fill her bucket (running half marathons and creating handmade jewelry), Sarah proudly dedicates time and a deeply personal approach to matching families and caregivers. In fact, she has built a reputation for creating meaningful, lasting connections, which is everything to nannies and the families they, simply put, become a part of.
Get to know Sarah who shares her journey through motherhood, entrepreneurship before AI assisted tech and smartphones, and the heart behind her growing platforms, including Nanny Playbook, a must for any family currently embarking on the nanny search, and The Nanny Union, just for nannies. Welcome, Sarah!
Hi Sarah! Give us a quick snapshot of you and your life right now.
Hi! Life is busy in the best possible way. I have been splitting time between Chicago and Austin for the last 10 years or so. I love the combo of Chicago’s seasons and Austin’s warmth! I lived in Chicago full-time for 12 years and had all three of my kids in the city. When they became school-aged, we moved to Austin for more space. I still spend time in Chicago and have a little apartment in Wicker Park. Thankfully, my business has remained in Chicago and I plan to move back full-time in a few years!
My days typically consist of making breakfast for my kids and going to yoga, or for a run. I work from home and spend most of the day on my computer, and occasionally hit a fun coffee shop or brewery! You’ll find me on the weekends making jewelry, going to a kid’s sporting event, or hanging out with my dogs (2 labs and an English golden).
Tell us about your family. What does motherhood look like in your house these days?
My kids are 19, 17, and 15. We have officially entered the era of college visits and are recently awaiting admissions decisions. It’s an exciting time, but also a bit nerve-racking. I’m anxious to know where I’ll follow my daughter to college and get a one-bedroom apartment because I’m afraid I’ll miss her too much! Maeve is a senior this year. My oldest son is in Wisconsin and has a passion for equine, and is finding his place, hopefully on a ranch someday! My youngest, Remy, is a sophomore. He’s sweet and funny and spends the most time with me…which I’ll take!
My partner has 4 kids of his own, so we have a lot of teens around! Seven teenagers have been a little nutty, comical, stressful, and fun all at the same time!
What’s something about you that might surprise people outside of your work and mom life?
I ran my first half-marathon in December. I had never really considered it, but a friend of mine asked me to do it with her, so why not?! It took a lot of training and time spent running, but the new Taylor album came out, and that was super helpful in getting through all of those miles!
I also recently started making jewelry. I used to do this when I was younger and decided I needed a hobby as my kids don’t take up as much of my time anymore. It’s been a nice creative outlet 🙂
What are you loving lately?
Travel! I’m 45, and I feel like the older I get, the more I think about traveling. My partner and I went to Italy last summer, and it was a dream. I’ve been to Europe a few times before, but that was in my 20’s, which was a much different trip given a major lack of funds! So this time, it was a much different experience. We went to Rome, Naples, Cilento, and Ischia. I want to tell you without telling you about Ischia because it’s not super well known…but the most amazing place I’ve ever been!
I went to Portugal this year on my friend’s yoga retreat, which was absolutely amazing. I loved Lisbon. And this summer I’m taking my daughter, Maeve to Paris…as promised, for her graduation present. My mom is coming too, and we’re getting matching tattoos (all three of us). So fun!
What’s something about motherhood, work, or balancing both that you wish more people talked about honestly?
The balancing act of motherhood. Wow, this question never seems to get answered. The last two years have been a challenge with one of the kids and their mental health. I won’t describe myself as a patient person, but I’ve grown much more patient over the last two years. The thing about motherhood is you really never know if what you’re doing is “right”. Somehow, you’re going to screw up somewhere; this is where the patience comes in. It’s inevitable that we can’t get everything right, so patience and a lot of listening are always a win.
Sarah, I love that very real and authentic answer, thank you. Speaking more on patience, is there a quote, mantra, or mindset that grounds you when things feel chaotic?
Seems like these days “Let Them” is everyone’s mantra, and I’m here for it:)
Definitely about that! It’s time to get down to business! Congratulations on celebrating 20 years of Olive You Nanny! Tell our readers all about your wonderful nanny placement services.
I started Olive You Nanny in 2005, 20 years ago! I had been a nanny, and started the company when I was 24 using a flip phone and Craigslist. I’d say we have come a long way! Olive You Nanny matches families with nannies who eventually become part of their families.
We have a unique approach to the process. I ask a lot of questions about parenting styles and personality types to really get a grasp on who I’m working with and how I can find a great fit. It’s not all about hours, pay, or vacation time. It’s really getting down to the core of who these families are and who will be a great addition, and to help their “ship” run smoothly.
I find that mutual respect, communication, and partnership really make these relationships successful. My favorite part of what I do is helping parents navigate the entire process from matching, interviews, and contracts, and making sure they have all their questions answered, and also being able to send them great candidates who blow them away!
Thinking back to the first year of business, what was that like?
That feels like a million years ago! I was so young, but I think that my age was really helpful because I just went for it. I spent a lot of time building a business plan, attending meetings at a non-profit for women entrepreneurs, and doing a ton of research. At the time, there were really only two other agencies, and my approach was much more personal. Now I’m sure you could easily use AI to craft a business plan!
You recently created a Nanny Playbook. What is that and how does it help families find the perfect nanny?
Social media has really reshaped what I do. I have spent a lot of time researching where families are and what they are looking for. Families can post jobs on Facebook nowadays, but I think a large part of the process is overlooked. Again, it’s not all about hours and pay, but about a match. It’s difficult to find a nanny if you have never done it before. I created Nanny Playbook, which is a guide to conducting your own nanny search. Think of it as having the expertise without really knowing anything about how to find a nanny!
Nanny Playbook is exactly what it sounds like: a playbook to ensure you are taking actionable steps in hiring a nanny. Nanny Playbook has interview questions, a guide to industry standards, a contract, and other helpful tools.
Nannies need connection and community as well, tell us about the platform you started called The Nanny Union and why that is so beneficial for the families that they serve.
Ah, this was a long time coming. If you’ve gotten this far, you know I’ve been working with nannies for over two decades. I love nannies; I love hearing their stories, talking about their ideas, what they value, and their struggles. I also coach nannies every day. When I’m interviewing them, I’m listening to what advice they need and what can be helpful. This is why I created The Nanny Union. It’s a place for NANNIES ONLY (so if you have a nanny, send them my way!)! It’s a place to build community, empower, share stories, and educate with our MasterClass and Portfolio Builder. We just launched, but I will soon have courses such as NCS, Doula training, nutrition, and sleep training classes for our members. It’s a hub for nannies, and I think it is needed!
Brilliant! How does Olive You Nanny service work from soup to nuts?
The uniqueness of Olive You Nanny lies in its attention to detail. I think a successful nanny placement is all about making sure that the family and nanny are a great match! There are a lot of unspoken things I pick up on during a consult with a family.
My goal is always to present the family with candidates that they never knew existed, and who can make their lives easier. I ensure that I send candidates who will be an amazing fit, and I encourage families to trust the process. I always know who is the best fit when I’m searching. This only comes with experience and being a people reader for a living.
After a family decides to move forward with their nanny, we handle all the employment details, including the contract, 6-month reviews, taxes, and more! And as I tell all of my clients: I’m always here!
Give us your dets! Where can we connect and ask questions?
You can find me:
Olive You Nanny, www.oliveyounanny.com
Nanny Playbook: www.nannyplaybook.com
The Nanny Union: https://community.thenannyunion.com/
About Our Meet a Mom Sponsor
Chicago North Shore Moms is supported in part by Mary Gregory Gifford, a 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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