About Trailhead Insurance Group

Know Who's Helping You Protect What Matters

Insurance decisions carry real consequences for your home, family, and business. You should know who you’re working with and feel comfortable asking questions before committing to coverage.

Trailhead Insurance Group serves individuals, families, and businesses across Montana and Wyoming, with decades of insurance experience across our team and access to multiple carriers.

Experience That Gives You a Clearer Picture

A price tells you what a policy costs. Understanding the coverage takes a closer look.

We help you work through the limits, deductibles, exclusions, and choices that affect what you’re buying. With multiple carriers to consider, we can compare coverage and cost against what you actually need to protect.

Whether you’re insuring your first home, reviewing business coverage, or protecting a more complex collection of assets, our role is to make those decisions easier to understand.

Yardley N.

ivensBillings Best Properties | Short-term Property Management

“Walk, don’t run, to talk to Trailhead Insurance Group about your insurance needs. A quick 10-minute phone call saved me almost HALF off my auto insurance premium. Paul and the crew genuinely care about you and what you actually need to be protected. And in this near-dystopian landscape of absolutely unhinged insurance rates, that matters. They’re honest, straightforward, and focused on finding what actually makes sense for you—not just making a quick buck off a commission. 10/10. Could not recommend them enough. Go talk to them. Your wallet might thank you. 😂”

Rob V.

Commercial Broker/Developer

“Just bound another one of my commercial property developments with my service oriented agent, Paul LaMantia. I do business with Paul because I like him and he makes it simple and convenient for me to do business with him. Give Paul a shout for any of your commercial real estate needs. He will take good care of you.”

Meet the People Behind Trailhead

Our team brings insurance experience and personal ties to the communities we serve.

Here’s a little about the people you’ll be working with.

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Paul LaMantia

Paul leads Trailhead with firsthand experience of how quickly circumstances can change when someone isn’t properly protected. His work includes years serving high-net-worth clients, adding perspective on the more complex needs that can come with significant assets.

He’s building the agency around a straightforward principle: put people before policies and recommend coverage that serves the client’s interests.

Outside work, Paul enjoys time with his family, walking his dog, being outdoors, working out, and playing golf.

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Kenzie White

Born and raised in Billings, Kenzie brings more than 10 years of insurance experience to the team. She focuses on getting to know her clients and explaining coverage in language they can understand.

Alongside her insurance work, Kenzie is a full-time college student. She enjoys community volunteering, football, golf, time with her dog, and ’90s country music.

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Jordyn Heimer

Montana has been home to Jordyn since he was two. A Laurel High School graduate, he returned after time away to the community that raised him.

As an insurance broker, Jordyn focuses on making coverage easier to understand so clients can make informed decisions about what they need to protect.

Outside work, he enjoys hunting, fishing, snowboarding, time at the lake, and being with family.

Start With What You Need to Protect

Tell us a little about your situation. We’ll help you understand the relevant coverage and the next step toward a quote.