Since our formation in 1989 we have kept your customer experience at the forefront of our operation. We understand the complexity of your insurance needs and are committed to explaining everything to you in a way that is easy to understand and makes sense. We all need health, auto, or home insurance. Allowing us to handle things not only ensures you’re getting the best deal, but it also comes at no extra cost! We are committed to serving you and want to be your point of contact.
If you’re nearing the age of 65, or you want to explore upgraded quotes for your home and auto insurance, or just have questions, give us a call. We want to help!


Kelly Jennaway is an owner at Jennaway & McLeod Insurance and has been in the insurance industry for over 10 years. He continues to assist clients with their goals and objectives in mind. He assists individuals, families, business owners and professionals with health insurance, income protection, retirement, and estate planning strategies to make their plan a reality.
Kelly is a Montana native who grew up on a ranch Northeast of Billings. Prior to joining Jennaway & McLeod Insurance, Kelly worked in pastoral ministry for over two decades. Kelly has lived in Bozeman for over twenty years. During his spare time, you can find him with family and friends as well as staying active with his dog Buddy.

Mike is the co-owner of McLeod Insurance and Financial Services and has provided a broad range of insurance and financial services to his clients for over 30 years. After graduating with Honors from Montana State University (MSU), Mike attended the University of Wisconsin Law School and practiced law for a short time before transitioning to the insurance and financial services industry in 1989.
Mike has served on multiple boards including President of the Bozeman Area Fellowship of Christian Athletes and Cru at MSU (formerly Campus Crusade for Christ). During his time at MSU, Mike played football for the Bobcats. He was on the team during the 1976 National Football Championship victory and was the Co-Captain when the Bobcats won the Big Sky Conference Championship in 1979. He later went on to play for the Edmonton Eskimos of the CFL and Green Bay Packers of the NFL. Mike married his wife Vicki in 1978 and they raised three children (Matthew, Mark & Mikaela) here in Bozeman.

Kyle Jennaway started in the insurance business in 2020 during his time living in Kalispell Montana. Since then, he has moved back to his hometown of Bozeman Montana to partner with his father Kelly Jennaway. He specializes in home, auto, and commercial lines insurance. Kyle is heavily involved with his community outside of the office. He enjoys serving at his local church, playing music with his friends, and you’ll be sure to see him at the gym before the sun comes up!

Though new to the team, Tanner is not new to the Gallatin Valley as he was born and raised in the area. Working previously as a pastor and middle school teacher, he has spent most of his professional life helping and serving others. When not working, he can be found serving in Sunday School or leading worship at his local church or reading a good book in the nearest coffee shop.

A Bozeman Native, Katie has enjoyed working at Jennaway & McLeod Insurance since 2022 as a receptionist scheduling and taking messages. Katie enjoys distance running, the symphony, and meeting new clients from the area. She provides a welcoming and comfortable environment from start to finish, to new and returning clients!