Navigate risk
with a partner
who knows the terrain
Trailside Risk Partners builds tailored coverage for businesses, builders, and families — guided by decades of expertise and a relentless focus on protecting what you've worked to build.
Protection mapped to every part of your world
Commercial
Property, liability, fleet, and umbrella coverage engineered around how your business actually operates.
Learn moreWorkers' Comp
Compliant, cost-controlled programs with a CWCA in your corner to manage claims and experience mods.
Learn moreConstruction (CRIS)
Builders risk, contractor liability, and bonding from a Construction Risk & Insurance Specialist.
Learn moreHomeowners
Protect your home, belongings, and liability with coverage that reflects true replacement value.
Learn moreAuto
Personal and commercial auto with the right limits, the right carriers, and claims support that shows up.
Learn morePersonal Lines
Umbrella, valuables, and specialty coverage that wraps around your whole financial picture.
Learn moreRisk Management
A CRM-led review of your exposures with a roadmap to close gaps before they become claims.
Learn moreAn independent guide, not a vendor
As an independent brokerage, we answer to you — never a single carrier. We shop the market, pressure-test your exposures, and engineer coverage that holds when it matters.
Built on relationships,
earned through results
Aaron Hennings founded Trailside Risk Partners on a simple belief: insurance should be a relationship, not a transaction. With designations spanning risk management, construction, and workers' compensation, Aaron brings rare technical depth to every client conversation.
He partners with each client to map exposures, close gaps, and stand beside them through every claim — so you can move forward with confidence.
A clear route from exposure to protected
Listen
We learn your business, your assets, and what keeps you up at night.
Map
A full review of exposures — finding the gaps before they find you.
Engineer
We shop the market and build coverage tailored to your real risk.
Stand by
Ongoing reviews and claims advocacy for the life of the relationship.
Ready to find out where you're exposed?
Start with a no-pressure conversation. We'll review your current coverage, flag the gaps, and show you what better looks like.