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Chris McClory

Licensed, independent insurance agent



Chris McClory is the co-founder and President of Milestone Medicare, LLC. He has over 20 years’ experience in the financial services industry. As an independent insurance agent specializing in Medicare insurance, Chris provides his clients with unbiased expert advice on enrolling in Medicare benefits as well as selecting Medicare insurance coverage based on individual client needs. His passion for working with and helping others is what drives him, which is also reflected in his ten years as a volunteer fire fighter and EMT on the Maple Lake Fire Department. He has three children and currently lives in Maple Lake with his wife Natalie after relocating to Minnesota from Arizona in 2006. What he loves most about Minnesota is fishing with his children and the changing seasons, although he says that after the novelty wore off, he could do without the long winters.

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Tammy Hendrickson

Licensed, independent insurance agent



Tammy Hendrickson has a background in public education and was an elementary school teacher in the area for over 15 years. Now a licensed, independent Medicare insurance agent, Tammy has a gift for working with beneficiaries to guide them to a better understanding of the sometimes complicated topic of Medicare.  Helping people is in her DNA.  Tammy grew up and has spent most of her life in Buffalo, MN where she now lives with her husband Jimmy, their three teenage daughters, two energetic dogs and a very patient cat. Tammy also coaches for the Wright County Wave Swim Club and works on the beach as a lifeguard.  


Becca Luebbers

Operations Manager

Licensed, independent insurance agent


Becca Luebbers is the Operations Manager for Milestone Medicare and is also a licensed, independent insurance agent. Becca's background is in customer service and business management.  She has developed a specialty in Medicare insurance plans, and now enjoys supporting the agent team at Milestone while also working directly with beneficiaries to help them make decisions about their health care coverage. Her focus and passion are providing exceptional service to our clients. 


Becca is a 2008 graduate of Annandale High School, and she attended St. Cloud State University where she earned her associate degree in 2012. She and her husband Sam live in Maple Lake with their two children Caroline (6) and Jack (5).  Although her kids keep her on her toes, Becca finds time to enjoy hiking, boating, snowmobiling, and reading; and she serves as a volunteer at the Maple Lake public library.  

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Natalie McClory

Licensed, independent insurance agent



Natalie McClory is the co-founder and Marketing Director of Milestone Medicare, LLC. She has over 20 years’ experience in training, speaking and event hosting. Her ability to communicate effectively and connect with people compliments her ability, as an independent insurance agent, to provide clients with unbiased expert advice on selecting appropriate Medicare insurance coverage. This experience also uniquely suits her for leading Milestone Medicare’s public training courses, events and overall marketing strategy. She returned to her roots here in Minnesota after a 17-year hiatus in central Arizona to be closer to family. Growing up in Buffalo, MN she now lives in Maple Lake with her husband Chris and her two children. She has a passion for Vikings football and enjoys being involved with her children’s sporting activities, maybe too much so according to her tween and teenager.