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Oliver Insurance

101 N Ivy St
Canby, OR 97013

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Featured Our Team

Our Team

Our Team


President – 503-266-2715 Ext. 605 | Email Ryan Oliver

Ryan Oliver

Ryan Oliver has been a member of the Oliver Insurance team for over 20 years. He is a UNLV graduate but always roots for the Oregon Ducks. A dedicated community leader, Ryan served as a member of the Canby Chamber of Commerce Board of Directors for 15 years, is currently the President of Canby Junior Baseball. When his father Wayne passed, he created the Wayne Oliver Foundation which benefits local youth sport programs and the ALS Association. He also serves on the CTV5 Board of Directors and the Canby Parks and Recreation Advisory Committee.

Ryan and his wife Kerrie live in Canby with their two sons, Maddox and Kellen. They stay busy keeping up with boys and their activities and they are avid Oregon Duck fans!


CSR & Personal Lines Agent – 503-266-2715 | Email Emily Bennett

Emily Bennett

Emily joined the Oliver Insurance team in July of 2022 after her graduation from Oregon State University. Emily is our front office Client Services Representative. Since joining our team, she has worked hard to pass her insurance exam and now is an official licensed agent. Emily has a passion for photography, travel and her two dogs, Vinnie & Floyd. She is fluent in Spanish and brings a positive, can-do attitude to our office. When asked if she prefers tacos or pizza, she says neither… it is pasta all the way!

Favorite Charity: CASA – Court Appointed Special Advocates


Business/Personal Agent – 503-266-2715 Ext. 607 | Email Kathy Clifford

Kathy Clifford

Kathy started with us in 2007 as a personal lines agent. She continues to work our personal lines and is known in the office for having all the right information at her fingertips. She is highly organized and we all reap the benefits. She also assists in our Business Insurance Team with renewals and customer service.

What Kathy loves the most is her adorable, growing family. She has two children of her own and now gets to enjoy being Grandma also! Spending time with her grandsons is top priority. She and her husband have been married for over 34 years and whenever they can, escape Canby life for camping life! Their favorite spot is Beverly Beach.

Fun Fact: Although a current Oregonian, she will always consider Butte, Montana her "home".


Business/P&C Agent - 503-266-2715 Ext. 609 | Email Brett Henry

Brett Henry

Brett joined our team in 2015. He began as a Personal Lines producer and continues to serve in that capacity. In addition to the P&C line, he now services our commercial clients and is helping build and restructure our Business Insurance Team.

Brett keeps a pretty full schedule outside the office with his wife Denise, and two boys, Issac and Elliott. He has coached high school basketball for over 15 years and is currently head Boys Basketball Coach at Evergreen High School in Vancouver, Washington. As an ASU grad, he is an avid Sun Devil fan and tries to visit Tempe at least once a year. In a life where he had more time, he would work on his golf game, hang out with his family more, and continue running a highly successful fantasy football franchise.

Favorite Dad Joke: "Some people say I have a dad bod but I see myself as more of a father figure."


Marketing & Operations - 503-266-8611 | Email Kerrie Oliver

Kerrie Oliver

Kerrie joined her husband, Ryan at our office in 2016. Kerrie handles the marketing and operations side of the business. She works on community involvement, client events, communication and overall office operations.

Outside the office, Kerrie is doing the mom thing with her two boys, Maddox and Kellen. There is rarely a shortage in sporting events to attend. She also enjoy relaxing with family and girlfriends...and she LOVES a good girl's trip for shopping and fun. Horses and animals in general are her other favorite loves!

Favorite Shows: Outlander, Stranger Things, Yellowstone, Ted Lasso

Favorite Charities: The Wayne Oliver Foundation, ALS Association, The Dougy Center, Canby Educational Foundation and Pass it On, Canby!


Business/P&C Agent - 503-266-2715 Ext. 606 | Email Kent Petterson

Kent Petterson

Kent joined Oliver Insurance in February 2019 with 10+ years insurance experience. He is an Oregon graduate and is always rooting for the Ducks. Community involvement is one of his passions. Currently he is involved as a PTA VP and Canby Micro Soccer Coordinator. Kent also organizes a golf tournament supporting local children’s charities (Golfing 4 Kids). Kent resides in Canby with his two sons, Kyle and Ryan. He loves to be outdoors camping, hiking and just staying active. He keeps busy with his boys’ different activities, as well as acting as their personal chauffeur.


Personal Agent - 503-266-2715 Ext. 606 | Email Bryan Thompson

Bryan Thompson

Bryan joined our team in April of 2022. Bryan comes to Oliver Insurance from the banking and customer service industry, where he spent the last 20 years. Bryan works on both the personal line and business line side for our office.
As a graduate of University of Oregon, he fits in very well!

Bryan and his wife of over 30 years, April, are Canby natives. He enjoys spending his free time camping while building and tending to the campfire. Bryan’s other area of expertise is music! He loves “slow jams” and puts together tailgate music for the Oregon Duck football games they attend during fall. Bryan and April have three grown children who are making their way in the world!

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