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Highlighted Nanny – Ashleigh Tennant

“We contacted Strollers and Stilettos looking for a full-time nanny to help with our three boys. I work a very odd part-time schedule and am home a lot, so I was looking for a team member who would be flexible and able to adjust to each day’s changing schedule. Ashleigh has been the perfect fit for our family. She shows up each day with a positive and cheerful attitude and somehow maintains the energy all day to not only watch our energetic boys, but to also pitch in wherever needed to help the family. If I am with the kids and she has some downtime she becomes wonder woman running around getting groceries, organizing the pantry, finding library books around the house, etc. Ashleigh is also amazing with the kids. They all love her and miss her on the weekends. Ashleigh is so good at understanding and implementing our routines and parenting preferences, so we feel there is always the same consistency and structure even when we are not home. Finally, Ashleigh is just a delight to have around. We have felt so lucky to have Ashleigh as our nanny and are grateful to Strollers and Stilettos for the placement.

– C.E. (Mother of three children in Winnetka, Illinois)


Strollers and Stilettos® interviewed Ashleigh Tennant as our highlighted nanny for the month of June. Ashleigh holds a degree in Advertising and PR from the University of Wisconsin-Milwaukee. Read the full interview below!


S&S: Where did you grow up?

AT: I’ve lived in several different states – Michigan on three occasions, Mississippi, South Dakota, Wisconsin and Illinois.I mostly consider myself from South Dakota as that’s where I lived the longest.


S&S: Why did you end up in Chicago?

AT: I ended up in Chicago after accepting a position to manage Abercrombie and Fitch at Woodfield Mall in Schaumburg.


S&S: What is your alma mater?

AT: I graduated from the University of Wisconsin-Milwaukee.


S&S: What degree(s) do you hold?

AT: I have a Bachelor’s degree in Advertising and PR.


S&S: Tell me a little bit about your professional experience – What have some of your previous roles been?

AT: I’ve held several management roles for Abercrombie and Fitch and Hollister before realizing that my passion involved working with kids. I’ve worked as a part time nanny for a year during college and after leaving my retail job, worked full time as a nanny to two young children.


S&S: What did you want to be when you “grew up”?

AT: I honestly thought I would become an elementary school teacher when I grew up but changed my mind once I realized how underpaid and under appreciated teachers are.


S&S: Who is one person you looked up to or still look up to?

AT: I’ve always looked up to my mom – she is one of the kindest and most caring people I’ve ever met. There’s honestly nothing she can’t do. Her drive to accomplish things on her own is very inspiring to me. She’s extremely independent and I believe most of my best attributes are a testament to how she raised me.


S&S: Why did you decide to become a nanny, house manager, babysitter, etc.?

AT: I absolutely love working with kids – I love watching them grow and learn. I toyed around with the idea of going back to school to become a teacher but the idea of developing a one-on-one relationship with a child and family appealed to me more.


S&S: How long have you been in this role?

AT: I have been in my current role for a year now.


S&S: What is your favorite part of your current position?

AT: I absolutely love how no two days are alike. I may get to work in the morning and find out that I’ll be spending most of my day running errands or doing organizational tasks or I could be taking care of all three boys, or just one of them. It keeps things interesting!


S&S: Why do you enjoy working with children?

AT: I love being able to see the world through a child’s eyes. I love watching them grow up. I love how curious and honest they are. I also enjoy being able to teach them different things. We constantly talk about currents events and things that are happening in the world. It’s a challenge to explain adult issues to young minds but I like being able to help foster an understanding of the world for them.


S&S: Kids often say whatever comes to mind – Do you have a favorite line from a kiddo you previously worked with?

AT: My older charges are always saying things that make me laugh but one of my favorites was from a conversation about whether or not we could drive from Chicago to Brazil. I said no but my five year old charge insisted that its possible because he read it in a book somewhere. When I said “But you can’t read yet so how is that possible?” He fired back with “Well anything is possible, Ashleigh!”


S&S: Do you want to have a family of your own someday? How many kids do you envision yourself having?

AT: I absolutely do – Ideally I’d love four kids… Realistically, probably two.


S&S: What are your favorite things to do with kids?

AT: I love to do anything that keeps them active! Outings to the playground, beach or library are always fun for us. I also enjoy taking them on bike rides or walks or even just drawing with chalk in the driveway.


S&S: What do you enjoy doing in Chicago during your personal time?

AT: In my personal time I love to read, go out to dinner, or see a movie. I spend a lot of my free time taking barre and Orangetheory classes and going to Costco. I have a very tame personal life!


S&S: Tell me about a day in the life of a Nanny.

AT: My day starts bright and early at 7am! With the help of their mom, we get all three boys fed and dressed. Then it’s drop off at school for the older boys. The toddler and I spend the most time together. We might have a class to attend or just play time. Depending on the day, I might run errands or do a specific organization task while Mom watches the boys. Afternoons are full of activities for the older boys which Mom and I usually divide and conquer together. We always have very busy and full days!


S&S: What are some of your favorite spots in the Chicago area (i.e. museums, play cafes, restaurants, beaches)?

AT: I absolutely love Tower Road Beach – It’s great for both adults and kids. I also love how Chicago has so many museums! The Field Museum is my favorite – I love the dinosaur exhibit.


S&S: Where do you see yourself in five years – On a personal and/or professional level?

AT: In five years I might be looking to start a family of my own so I’m considering running an in-home daycare so I would be able to raise my own children while also working a job that I love!


S&S: How did you hear about Strollers and Stilettos™?

AT: I actually found Strollers and Stilettos while looking for positions on a different websites. Katie had posted a position and asked me to apply through the site. I had been toying with the idea of using an agency to help find a position, but was not sure where to start. Katie was very quick to respond to my application and answer all my questions.


S&S: What was the process like with Strollers and Stilettos™?

AT: So easy! Katie is one of the most efficient and organized people I have ever worked with in my life. She really went out of her way to meet with me at a time that worked with my schedule! We were able to create a sort of fact sheet about myself – personality and experience with just one meeting. I didn’t need to ask Katie for extra information or forms, she was so quick to send things to me right away. She’s so helpful!


S&S: How did Strollers and Stilettos™ help you with finding a family in Chicago?

AT: Katie really emphasizes finding the right fit for both the family and the nanny. She already has a good idea of which candidate is right for a family so it really takes the guess work out of it on my end. She made sure that all my needs were met which was extremely important to me and my career.


S&S: Do you have any advice for families interested in hiring a nanny?

AT: Definitely use an agency and schedule trial runs! This will eliminate a lot of future issues that could arise. You’ll know your nanny has passed thorough background checks and you’ll know how she/he interacts with your kids. Look for someone who is interested in longevity as well, so a relationship with your kids and nanny can really flourish.


S&S: Do you have any advice for candidates interested in becoming a nanny?

AT: Also, use an agency and know your worth! A liaison is very helpful when it comes to getting a written contract and protects you from being taken advantage of! The families looking for a nanny have all been screened and interviewed as well which gives you a sense of both job security and safety!