Welcome to JM Insurance Group

We've got you covered!

We are committed to great customer satisfaction. Stop by and visit, call us, or request a quote today!

JM Insurance Group specializes in writing home, renters, landlord, auto, umbrella, motorcycles, ATVs, boats, or any other toys or unique items you may own. We have several types of personal insurance to cover all of your individual circumstances.

We are an independent agency that offers a full range of insurance products from several A-rated or better companies. This means you don't have to change agencies as your insurance situations evolve.

Understanding insurance can be quite complicated. At JM Insurance Group, we believe in explaining the options to you so you can make an educated decision on the route you would like to pursue. We encourage a face-to-face visit for the initial meeting to explain coverage and address any insurance gaps you may have. We will do a periodic review every couple of years since life happens and things change.

The companies we represent are great at handling claims. However, the claims experience can be confusing, and we are here to help guide you throughout the process.

Old, blue truck with JM Insurance Group logo on door

Meet Our Team

picture of jennifer massey


“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 make a big difference in 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 Masters of Insurance.

photo of 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 right steps to make sure that customer leaves satisfied.

Aside from her newfound love of the insurance industry, Maddison also dedicates her spare time towards 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 not stop until she knows her clients are happy.

photo of brian


Born in Florence, Brian is a Montanan local who has transitioned from the banking and lending channels into the insurance industry. Eager to help clients, he joined us in September of 2022 and is an asset to our team. He is an optimistic agent, passionate about extending a helping hand to others whenever possible.

Brian is a family man, and he enjoys spending time with his wife and children outside of work. This includes engaging in activities that strengthen their family bonds. Brian’s family extends past his human children, as he also cares for the family golden doodle, Wrigley, and their fish and toad. He is an avid sports fan, his favorite baseball team being the Cubs and his favorite football team being the Broncos.

photo of Lydia


Lydia Brester is a trusted insurance professional with a heart as big as the Montana sky. She joins 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 in her spare time, she enjoys crafting. With every decision that Lydia makes, she 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.

Community and News

Since JM Insurance opened its doors in January 2017, our major emphasis has been community involvement. We are dedicated to helping through volunteering, collecting supplies for various programs, and monetary donations. We help many charities with a focus on local charities in Montana. We are a small agency but have a big heart! If you would like to be involved or would like to participate in a donation to one of our charities, please email jennifer@jminsgroup.com or call at 406-534-8008.

Red Lodge Flooding

In June of 2022, JM Insurance Group donated 21 cases of water to Red Lodge after flooding left part of the town without drinkable water. Jennifer volunteered for a couple of days, handing out snack bags to workers and homeowners affected by the flooding. She also delivered breakfast to the Red Lodge Fire Department.

Donating 21 cases of water to Red Lodge
Dropping off breakfast for the Red Lodge Fire Department


Dale Morgan, a former homeless man, is doing what nobody did for him by offering homeless people blankets and other winter clothing. This effort of Dale's received media coverage and many articles in the Billings Gazette. JM Insurance provided a drop-off location in the heights for the various clothing and blankets. With all of the support of the heights community, we were able to donate several large bags of blankets and clothing.

1st donation pickup with Dale Morgan
Stephanie, a teacher, picking up the donations


Many students and families in a few elementary schools around Billings are low-income. They struggle to provide adequate clothing and school snacks for their children. JMIG purchased some snacks for these students.


JM Insurance Group raffled a Ringo Lake Quilt made by breast cancer survivor Wendy Negethon. We raised money in donations for three cancer programs, Relay for Life, Pack the Place in Pink, and PEAKS.

Emilie, winner of the Ringo Lake Quilt
Downtown Billings Alliance - Alive After Five


Every Thursday in the Summer, Jennifer volunteers for the Downtown Billings Alliance for the Alive After Five event. The DBA is a non-profit organization with a vision to achieve excellence in community leadership and growth. Our Mission is to develop a strong business climate and vibrant economy by serving the community in a leadership role, thereby enhancing the quality of life.


During Yellowstone County's Relay For Life, JM Insurance Group sponsored a team to walk for the event in 2017 and 2018. The mission of Relay for Life is never to forget those lost to cancer, that those who face cancer will be supported, and that one day, cancer will be eliminated.

2017 Relay for Life group
Jennifer modeling an outfit for the fashion show.


The fight against breast cancer is near and dear to our hearts as Jennifer Massey, owner of JIMG, is a breast cancer survivor. Anyone diagnosed with breast cancer can apply for assistance with Pack the Place in Pink. In October, during Breast Cancer Awareness Month, they have a fashion show at the biggest mall in Montana where all the models are cancer survivors.

Pack the Place in Pink Breast Cancer Survivors


JMIG had a team for the Alzheimer's Association Mulligans for Memories golf tournament at Briarwood golf course in July 2017. This fun golf scramble is a great way to enjoy the summer while raising funds, concern, and awareness in the fight against Alzheimer's.

Jennifer and co-golfer in front of the benefit's sign.
Golfing for Alzheimers Association's Mulligans for Memories

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  • JM Insurance Group
  • 513 Hilltop Rd, Suite 7
  • Billings, MT 59105