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 used to volunteer with the Billings Downtown Association. She is a breast cancer survivor and dedicates her time to many cancer affiliated organizations. The last few years, Jennifer has become a world traveler and spends her summertime with outdoor activities and going to Mustangs games. Jennifer loves football, go Seahawks and Bobcats!
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 Cross joined the insurance industry in 2021, wanting to help her family’s agency and driven by a desire to grow professionally while helping others. She is known for her insightful, solution-oriented approach, taking the time to listen actively, think creatively, and advocate on behalf of her clients to ensure they receive the best possible outcomes. Whether it’s discovering valuable discounts or guiding clients through the claims process, Maddison is responsive, detail-oriented, and committed to going above and beyond in her service.
Outside of the office, Maddison enjoys oil painting, reading, baking, and crafting, and brings that same creativity into her professional life. Her background includes roles in customer service and care, which further shaped her dedication to supporting others. Prior to committing to a career in insurance, Maddison was pursuing employment in the medical field. Montana born and raised, Maddison has an intimate understanding of the community as well as the communities surrounding Billings.
Karie
Having navigated the world of business ownership herself during her own ventures, she understands the importance of having a reliable agent in her corner. She is here to bring an optimistic and helpful approach to ensuring you have the peace of mind you deserve!
Alissa
Alissa Smith brings a thoughtful, client-focused approach to the insurance industry, shaped by both her professional background and her life experiences. After spending three and a half years as a stay-at-home mom, Alissa transitioned into insurance, drawing on her previous work in medical billing and her passion for helping people navigate important financial decisions. She discovered that the same attention to detail and care she valued in healthcare services translated perfectly into home and auto insurance.
What Alissa enjoys most about her work is the opportunity to connect with clients and truly understand their unique needs. She takes pride in solving problems, finding the right coverage, and helping individuals and families save money while protecting what matters most.
Before entering the insurance field, Alissa held a variety of roles that strengthened her communication and leadership skills, including Assistant Manager at a theater, HR Manager for a home care company, and Account Manager at a medical billing company.
Outside of work, Alissa enjoys gardening, crafting, and painting. She’s also an accomplished home cook who loves preparing meals from scratch. A Montana native, she enjoys life with her three children, their dog Daisy, and a couple of unique companions—a frog and a snail for her youngest son.