Meet Our Team

At Prineville Insurance Agency, we've built our team with individuals who have the highest standards for client communication and servicing. No matter who you interact with at Prineville Insurance Agency, you'll have the best experience possible.

Monica Elsom

Owner

Monica has owned Insure Pacific Inc./ Prineville Insurance Agency, since 2008 and Insure Brookings, LLC/ Gerald Ross Agency, Inc., since 2013. Am proud to have such a great team that works together, by my side.

Also, volunteers as the board chair at Rimrock Trails Treatment Services. Being able to make a difference in people's lives, is what drives her the most!

Monica has two beautiful kids. A son in high school and a daughter at Linfield University. Personal time is filled with travel to swim meets, baking, and friends. We love to enjoy all that Central Oregon has to offer.

Meet Monica

Elaina Huffman

Vice President

The Vice President of the agency, Elaina has been on the Prineville Insurance team since 2006. She is a lifelong learner, maintaining her Certified Insurance Counselor (CIC) and Agriculture Farm Insurance Specialist (AFIS) designations. In 2017, Elaina created a division of the agency to focus specifically on the farm and ranch business.

Her husband, Jake, is the Vice Principal of Crook County High School. Together they have four children and run Central Oregon Wrestling Academy – a private wrestling academy focused on youth development.

Elaina loves her family, horses, her dog, being active, cookies, and wine.

Meet Elaina

Holly Hills

Agent

Holly is a Native Oregonian and has been in the Insurance Industry for 18 years; 15 years in Commercial lines working closely with Contractors, Non-Profits and Manufacturing risks. When Holly is not working, she loves to spend time with her two grandchildren in Northern California and to go RV’ing or to the Ocean Beaches with her husband and two dogs.

Meet Holly

Joy Wilson

Agent

Joy has been in the insurance industry for 13 years with a background in personal lines insurance. She enjoys working on farm & ranch business also.

Her hobbies are skiing, snowshoeing, hiking, kayaking, rafting, gardening, and traveling.

Meet Joy

Karla Sanders

Accounting

Karla has lived in Central Oregon most of her life. I enjoy the beautiful scenery, hiking, riding horse and reading. I’ve been working at Prineville Insurance since April 2014.

Meet Karla

Dawn Jackson

Agent

Dawn is originally from Iowa but, had also lived in Bend for 20 years before moving to the small town of Crane, Oregon. Dawn came to Prineville Insurance with 10 years of Insurance experience in Personal Lines and is currently exploring the Farming aspect of the insurance world. Farming, fishing, hunting and her community are her passions, as well as servicing her clients with first class customer service.

Meet Dawn

Sabrina Stout

Agent

“After growing up in and around the insurance industry, Sabrina became a licensed insurance agent in 2016. In 2019, after graduating from Portland State University with a bachelor’s degree in the English and Spanish languages, she decided to pursue a career in which the focus was helping others. Now, with ample knowledge in life insurance, health insurance, and Medicare—as well as a skilled and experienced team standing beside her—Sabrina knows she has found the career she had been searching for.

While not working, Sabrina spends as much time as she can outdoors. With a passion for fishing, dirt bike riding, backpacking, snowboarding, and finding all the hidden gems that Oregon has to offer, there is no other place she’d rather call home.”

Meet Sabrina

Alex Holsheimer

Agent

Alex is experienced in project management, fundraising, B2B sales, and client development across a broad range of sectors. Working in both personal and commercial lines, Alex takes pride in offering insurance solutions to clients and earning their repeat business. He has raised over $9m in funding for private, public, and non-profit projects, and co-owns a small coffee farm. Having grown up near agriculture, Alex loves small towns. He is an avid traveler, enjoys craft beer, and explores the beautiful outdoors and plentiful recreational activities in Central Oregon.

Meet Alex