Dynamic Teamwork
Serving Montana Since 2017
Based in Billings, MT, JM Insurance Group offers a wide range of personal insurance options—home, renters, landlord, auto, umbrella, motorcycle, ATV, and boat coverage—through top-rated companies. As an independent agency, we tailor flexible solutions that evolve with your needs, starting with face-to-face meetings to review your policies and identify coverage gaps. We’re committed to helping you understand your options so you can make informed decisions. While our partner companies manage claims efficiently, we can guide and support you throughout the process.
At JM Insurance Group, we’re more than a team – we’re a dedicated family driven by excellence, integrity, and personalized service. With a blend of seasoned veterans and emerging talent, we offer tailored insurance solutions to meet evolving needs, prioritizing your interests and fostering meaningful connections.
Our collaborative approach ensures exceptional service and results for both clients and our team. Committed to continuous growth, we stay ahead of industry trends while actively supporting local communities. Choose JM Insurance Group as your trusted partner in protection, and let’s navigate life’s uncertainties together, safeguarding what matters most and building a brighter future.
Meet The Team!
Jennifer
“In 2017, I started my new agency. In just a short time, it has grown from one employee to several employees. My passion is saving clients money and getting them the best insurance policy tailored to their situations. Choosing the right insurance agent can significantly affect price, service, and headaches!”
Jennifer Massey, owner of JM Insurance Group, was introduced to the insurance industry in 1996, selling life insurance as an internship in college. She also worked part-time for a captive insurance agency, assisting home and auto policyholders. She was a financial adviser and a mortgage lender before starting her career in personal lines in 2005. Jennifer is active in the community, serving on several boards of directors, including Rebuilding Together, The Family Tree Center, The Festival of Trees, and currently volunteering with the Billings Downtown Association. She is a breast cancer survivor and dedicates her time to Relay for Life and the Pack the Mall in Pink event. Her summertime is spent camping, hiking, fishing, and going to Mustangs games. She plays softball and is serious about watching NFL football!
Jennifer graduated from Montana State University with a marketing degree. She has her AINS designation for general insurance and is working on the CPCU designation, which is, in a sense, a Master’s of Insurance.
Maddison
Maddison joins us in the Spring of 2021 as a full-time, licensed insurance professional determined to find the best possible coverage for your needs. She specializes in personal and commercial lines. She takes great pride in getting to know clients and taking the proper steps to ensure customer satisfaction.
Aside from her newfound love of the insurance industry, Maddison dedicates her spare time to oil painting and enjoying the great outdoors.
Maddison is eager to help clients save money while finding them the best fit for their coverage needs and will stop at nothing to ensure that her clients are happy.
Lydia
Lydia Brester is a trusted insurance professional with a heart as big as the Montana sky. She joined us in the Spring of 2024. Born in West Virginia but raised in Michigan, she found her true home here in Montana in 2006 and has never looked back.
As a devoted boy mom, she knows the value of protecting what matters most. From mid-March to the end of October, you’ll catch her cheering at the diamond or excitedly watching from the 50-yard line. When she’s not occupied with the world of sports, she enjoys motorcycle rides accompanied by her husband of eleven years.
She treasures family time and enjoys crafting in her spare time. With every decision she makes, Lydia strives to create a legacy that her children will be proud of.
Lydia is a well-rounded agent licensed in Property and Casualty, Health, Life, and Surety insurance. She brings over a decade of insurance expertise to the table. Being a down-to-earth person, Lydia will always give it to clients straight, allowing them to make informed decisions they can understand. She is driven to do right by all the customers that she serves.
Karie
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