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Funeral Details – Chicago Jewish Funerals
Stephen Earl Applebaum. Beloved husband of Lily nee Rauchwerger. Loving father of Reuben Apple, Lauren (Adam) Tock, Jessica (Jeff) Merar and the late Benjamin Applebaum. Proud grandfather of Marley, Dylan, Sienna and Izzy. Dear brother of Ira (Evy) Applebaum and Raymond (Ellace) Applebaum. Service Wednesday 12 Noon at Chicago Jewish Funerals, 8851 Skokie Blvd (at Niles Center Road), Skokie.
Interment Sunset. In lieu of flowers, memorial contributions may be made to The Dragonfly Foundation Chicago. 833 Central Avenue, #1306. Highland Park, Illinois 60035 tinyurl.com/SApplebaum. To attend the funeral livestream, please visit our website. Arrangements by Chicago Jewish Funerals - Skokie Chapel, 847.229.8822, www.cjfinfo.com
The Passing of Stephen Applebaum
It is with deep sadness and tremendous gratitude that today's newsletter is dedicated to Stephen Applebaum who passed away on May 17, 2026, surrounded by his loving family. OBITUARY
I first met Stephen back in 2019 at what is now known as the Connected Claims event in Chicago. Stephen was a master at bringing people together for common causes and the P&C industry and claims were at the center of his influence. So, he launched an annual conference gathering thought leaders from around the globe for the betterment of the industry. Connected Claims Conference was later acquired by Reuters.
Following the 2019 conference and being thoroughly impressed, I made a point to get to know Stephen better since I was building my own consulting work after 34 years in the insurance carrier space. My approach was offering an article for Stephen's newsletter which was yet another way he would reach and connect to others. Anyone who knows Stephen would agree that helping and lifting up others was just his way of being.
Long story short, he liked the article, published it and invited me to work together. Fast forward, we enjoyed nearly seven years of serving clients in the P&C ecosystem, co-authoring thought content and co-curating this very newsletter, 'Connected'. Stephen made this time most rewarding and meaningful in so many ways from networking to creative solutions.
Stephen's storied career took shape after some initial accounting work (which he later shared was "boring") and became an executive with CCC Information Services in the early days of the company. After 17 years he went on to working with ADP (Solera), launched the company ClaimForce, Inc., joined Aite -Novarica Group and supported Waller Helms Advisors while operating as Managing Partner/founder of Insurance Solutions Group. While this summarizes Stephen's remarkable path, it better illustrates his energy, passion and relentless work ethic.
Although many plan retirement, Stephen openly admitted this was not his "strong suit". He would jest, "I failed at retiring at least 4-5 times". Instead he forged ahead, inspired others and never missed an opportunity to tackle the next challenge. To say Stephen touched a lot of people, would be a huge understatement.
Greater than Stephen - the professional, he was the kind of person who will forever be remembered. Stephen was a supreme listener and not only would take the time but truly cared to make sure he captured every detail. Always present. He had a sharp wit and brilliant mind which was clear and obvious in both business and life. Stephen's wife Lily and family, being together and fun times he enjoyed with grandchildren were most precious.
Stephen was an all-around terrific person, family-first, help others always, spirit. May his memory be a blessing to his family and all who knew him.
I am honored to call him a dear friend and colleague. I miss you already Stephen.