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Our Story

Hillock Insurance Group is a locally owned, full service agency dedicated to doing what’s best for clients. Carrying on the values of this community-owned business since 1999, Hillock Insurance protects individuals, families, and businesses. By offering all forms of health and life, property, and casualty insurance, we pride ourselves on making it simple and convenient to find affordable insurance that meets our clients’ diverse needs.

Hillock Insurance was founded by Kathleen and Leroy Bennett as "Bennett Insurance" in 1999. Hailie and Jared Hillock purchased the agency in 2014 to carry on their legacy of care and compassion for insureds. Through several rebrands, two office locations, and broadly expanding our list of carriers, our core has always stayed the same: To bring excellent service to the community we love.

The Hillock Family
The Hillock Insurance logo

An Homage to the Mountains

Owner, Hailie Hillock, has spent her entire life in Wallowa County and has grown a passion for exploring the majesty of the surrounding mountains. The mountain featured, Sacajawea Peak, not only reflects that, but also the value and strength of community. Unexpected times and occurrences require support and it means a world of a difference to be able to reach out to someone close, someone you know, and someone that understands where you are coming from.

Sacajawea Peak's namesake was a Lemhi Shoshone woman who, at 16, helped the Lewis & Clark expedition as a guide and interpreter through their journey. The Hillock Insurance team helps clients navigate too: from determining the best protection to helping as guides through challenging times.


Our logo reflects the beauty of our Wallowa Mountains and our promise to you. It's an honor to be trusted with supporting the most important areas of our community's lives.

Hailie Hillock

Owner, Property & Casualty Agent

Born and raised in Wallowa County, Hailie Hillock knows how important it is for locals to get help from other locals that truly understand their needs and are willing to go to bat for them. As the Co-Owner and Principal Property & Casualty Agent, Hailie uses this mindset to guide her day-to-day work. Whether she’s providing a quote or aiding an insured through the claims process, you can count on Hailie to go the extra mile to make sure you’re getting the best rates and truly understand your coverages.


Deeply connected to the agency, Hailie worked for the former owners, Leroy and Kathleen Bennett, for four years before purchasing the agency with her husband, Jared, in 2017. As a young agent, the Bennetts instilled in Hailie their care and compassion for insureds, and she carries on their legacy to this day. Hailie has now been a licensed agent for over 5 years.


Prior to insurance, Hailie worked for the United States Forest Service. She then went on to cleaning and maintaining trailheads for the Wallowa Whitman National Forest. Although her job isn't outdoors anymore, you’ll often find Hailie hitting the slopes backcountry skiing or enjoying the views from Wallowa County’s most challenging hikes on the weekends.


In between running a successful business and filling life with memorable adventures, Hailie never misses an opportunity to support her community, donating to nearly every fundraising event in the area. She also enjoys volunteering at the Elks Christmas Basket, Wallowa County Fly-In, Wallowa County Fair, and the Chief Joseph Days Rodeo.


Hailie is a proud mama to her step-daughter, Ella, and her three young boys, Johnny, Cash, and Jett.​

Hailie Hillock, Property & Casualty Agent, Owner of Hillock Insurance

Kathleen Negus-Bennett

Life & Health Agent, Medicare

Kathleen Negus Bennett is a long time resident of Wallowa County and former owner of the agency, back when it was Bennett Insurance. She and her late husband, Leroy, founded the agency with a focus on clients, promising a friendly and helpful experience. Although she had planned on retiring in 2017 after selling the agency to the Hillocks, Kathleen loved her work and clients so much she couldn’t bring herself to retire just yet. Without losing an ounce of spunk or charm, she has spent the last several decades helping folks in Wallowa County and the surrounding areas navigate the complexities of Medicare.


Kathleen has recently tapped into her love of traveling again, exploring the East Coast, Alaska, and more. Although she loves soaking in the new views, her favorite destinations are Texas and California where she gets to visit her two sons, their spouses, and children. An ever loving and patient caretaker, Kathleen also enjoys babysitting Hailie’s boys, John and Cash – she even invited Cash to be in her headshot!

Kathleen Negus Bennett.jpg

Susanna Bonnifer

Life & Health Agent

Susanna Bonnifer grew up near Pendleton, OR. After spending a few years in Oklahoma in Sales and Administration, the mountains called her back home. As a Life and Health Agent specializing in life insurance, Susanna focuses on building strong, long-lasting relationships with clients. Her friendly and helpful attitude shines through in all interactions whether they’re in-person, on the phone, or via email.


Fueled by dark roast coffee and a love of spontaneity, Susanna often spends her time outside and frequently walks or rides her bike to work. Although she’s relatively new to the County, she’s eager to make positive contributions to the community.

Vixen Radford-Wecks

Community Health Worker and Enrollment Specialist

With a never-ending passion for helping others, Vixen Radford-Wecks helps individuals and families understand and access health insurance. She is a Community Health Worker and Enrollment Specialist for the North East Oregon Network but works in-house at our agency to offer convenient services to our community.

Vixen knows her way around She is especially adept in Oregon Health Plan (OHP) and Children's Health Insurance Program (CHIP).

Vixen Radford-Wecks, Community Health Worker and Health Insurance Enrollment Specialist

Let's Work Together


209 Hwy 82 Enterprise, OR 97828

Mon - Thur


9:00 AM - 4:30 PM

9:00 AM - 3:00 PM

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