Meet a Mom: Meet Alexandra Eidenberg! | Chicago North Shore Moms

Hello friendly faces! It’s that time of the week! We’re back with a new CNSMoms’ Meet a Mom spotlight brought to you in part by Mary Gifford of Gifford Law. This week’s Meet a Mom interview is with Alexandra Eidenberg who is a Wilmette mom of four young kids and the founder and president of The Insurance People, an agency that specializes in employee benefits, individual health insurance and medicare along with all the bells and whistles to match like dental, vision, life, disability, and more.

It’s currently open enrollment season with health insurance, which means that Alexandra is uber busy. Still, this career-driven mama carved out some time to chat with CNSM. How does she balance this plus the impressive list below of personal and professional accomplishments? Her mantra: “The more you do, the more you can do mentality.” And through all of the craziness day-to-day she wouldn’t change it for the world. She proudly states: “Being a business owner has allowed me flexibility that not everyone has… I can work the hours I want when I want, and show up for my kids when they need me, or when I need them.”

Alexandra is kind, full of energy and the someone you want on your team. Welcome, Alexandra!

Hi Alexandra! Please introduce yourself. 

Hello there, I’m Alexandra Eidenberg. I was born and raised in Chicago and thought I would always be a Chicagoan but 4 kids later we are in Wilmette loving life.


You’re a mama! How many kiddos do you have and how old are they? 

We have 4 amazing kiddos. Nine year old identical twin girls, our middle guy is 7, and our little guy is 5. We are a big soccer family and spend most of our days schlepping between fields for various games and practices. Between work, community engagement and 4 kids the hustle is super real at our house.



Any fun facts about you?

Ooooooo, fun facts about me. I mean, not much, hmmmm. I love to cook and serve. I always tell folks to come on over, sit and look pretty and then I cook and clean while they enjoy themselves. I am all about hosting parties! I am also a runner and I super appreciate a good quiet morning, my feet on the ground, and clearing my mind, but rather filling it with the things I have to do and want to do. Kinda like daydreaming on the go.


I’ll be over for dinner tomorrow (LOL)! What are your favorite local places to spend with the family?

We are uber outdoorsy so if it is walks in the neighborhood, bike rides to local parks, or finding the nearest canoeing experience we are all in! In the summer we can be found beach bumming at the Wilmette beach and I am a massive lover of being in the sun. We also appreciate food a lot so eating out is always one of our favorite activities. Lulus in Evanston, Sophia Steak in Wilmette and Fred’s Garage in Winnetka are a few of our regular favorite spots. We also frequent Starbucks more than I would like to admit and all my kids have their own fav items — HELLO steamed apple juice.


You are the founder of The Insurance People. Tell us about your career path. What made you go out on your own?

I started my career in retail and loved working for Gap Inc and Limited Brands but I quickly learned that I was working like a dog to just make more money for corporations that did not care about me or my life goals. During my time in retail I loved connecting with people and learned my core genius is sales. I knew that I wanted to do something where I had a direct connection between my work ethic and income level.

I found insurance and never looked back. Fast forward 18 years later I am still at it and have had my own agency, The Insurance People, for 12 of those years. No one ever dreams of being in insurance, it is the ultimate in boring, but I like to think we make it fun and exciting. As I grew in the industry I found myself and my footing as a woman in a male dominated industry. I went from trying to fit the mold to creating a new path that is not only a place for me to thrive but for my staff to thrive too.

So, today I own The Insurance People, a fast paced, nearly all women, agency that specializes in employee benefits, individual health insurance and medicare along with all the bells and whistles to match like dental, vision, life, disability, and more. We are located in Skokie off the highway at Old Orchard Road and we do all your favorite boring things all while managing kids, engaging in the community and working our hardest to help folks find the right insurance, at the right time within their budget.



How do you have time for a full-time job and four kiddos? What outside help do you have to help manage your work/life?

Ha! Before having kids I used to do a lot of public speaking on work life balance. I had all these bright ideas and charts for folks to thrive. Then I had kids and was like “what the hell was I talking about” and realized that the only way to succeed as a working mom is to hit it hard, know when to say no, and to live every day like it could be the last. Not everyone likes the crazy hustle but I thrive from it. My personal mantra: The more you do, the more you can do mentality.

Being a mom is definitely the hardest job I have and I love my kids to pieces, but they drive me absolutely insane and I think it is that insanity that keeps me chugging along. I am in a constant state of begging little people to put on their shoes, to get in the car and to tow the line. I run a tight ship and my kids know that I mean business no matter what we are doing – on the field, at school, at an event, while I am on a client call, all of it.

Being a business owner has allowed me flexibility that not everyone has. For instance, I take meetings with my kids with me, and I do not care if they are chatty while I am on the phone. I can also turn away business that is not the right fit for my team and me. And mostly I can work the hours I want when I want, and show up for my kids when they need me, or when I need them. The only way it is possible is because my husband, Rog, and I know when to lean on the other. We make a great team and I am uber grateful for him and his ability to embrace the craze.



What do you want us to know about open enrollment season. Why is this so important?

Open enrollment season is the best time of year! Just kidding, but it does coincide with the holidays. Open enrollment season is a time period where you can enroll and make changes to your insurance for the January 1st start date. Many folks like having their deductible year match their policy year so the vast majority of folks renew, make changes and enroll during this time. Depending on the part of the market there are windows where you can make changes and only during that time can you make changes.

Open enrollment in the under 65 market is 11/1 – 12/15, medicare is 10/15 – 12/7 and small groups are 11/1 – 12/31 for the January start date. Groups can buy at any time during the year, medicare has several additional windows in the beginning of the year and under 65 individual has a second window 12/16 – 1/15 to enroll for February. At The Insurance People we enroll thousands of people within these windows and then all year long groups or folks with special enrollment periods (SEPS) coordinate with us. We help the same amount of folks October – December that we do January – September and this is because the vast majority of folks renew and make changes to match the calendar year.


What are your most proud professional and personal accomplishments?

We’re excited to announce that The Insurance People have achieved national recognition from CMS as Elite members of the Marketplace Circle of Champions for 2023 after helping more than 100 consumers enroll in Marketplace coverage during Open Enrollment.

A few additional personal and professional accomplishments:

  • LiftUpLift Ally 2017
  • Woman to Watch eWomenNetwork 2015
  • Blue Cross Blue Shield Blue Leaders 2020, 2021, 2022
  • Illinois Democratic Women (IDW) Woman of the Year 2020
  • ARISE Suburban Recognition Award 2019
  • In Her Shoes Woman of the Year 2018


Is there anything else you’d like us to know about?

I love coffee and organic wine and when it is not open enrollment I love frequenting our local chamber events and coordinating opportunities for women business owners to connect. During open enrollment we work with our clients exclusively via phone and I can’t wait to see folks in person again!!


What is the best way to reach you for more information?

Email is always the best way to reach me. [email protected]. You can learn more at or call us at 773-697-8082 too though. You can also follow us on Facebook and Instagram for updates.


About Our Meet a 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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