The Team

Health Insurance Strategies is an out-of-the-box thinking independent brokerage located in Bend, Oregon. Our personalized approach and education first style sets us apart in the industry. We enjoy working with Medicare and group clients who share our ideals of integrity and honesty and want to form a partnership that lasts well into the future. 

Andrew Gurbada, MBA

Oregon License: #19342466

At the office:
Andrew founded an insurance agency called SmarterHSA (www.smarterhsa.com) in 2016, which provides Employee Benefits and Medicare expertise across several states. SmarterHSA, LLC acquired HIS in April of 2026. He has over 15 years of employee benefit and Medicare experience.

Andrew holds a Master of Business Administration (MBA) from Hamline University (MN) and A Bachelor of Arts (BA) from Saint John’s University (MN).

Outside the office:
Andrew likes to spend time outdoors with family and friends. Andrew is married and has three young children.

Trey Deslauriers

Oregon License: #20630005

At the office:
Trey works in both Employee Benefit and Medicare sales, drawing on the experience and creative thinking of the HIS team to continue to expand his knowledge base in the industry. Trey brings with him a diverse background as an entrepreneur, as well as holding various sales & management positions within the residential and commercial real estate sector.  

Outside the office:
Born and raised in Anchorage AK, Trey occupies his off time with Hockey, Curling, and Skiing. Once the weather warms you can find him on the biking trails or out on the golf course.

Don Klippenes (Retired)

Oregon License: #6224586

At the office:
Don has retired from HIS, effective April 2026. As the founder of HIS, Don held over 30 years of experience working with Medicare and group individuals using an education first approach and forming a relationship with every client. He was a member of NAHU and has been involved in lobbying health issues at both the state and federal level for many years.

Outside the office:
Don loves spending time with his kids and grandkids, golfing, skiing, or walking with his buddy Charlie.  

Charlie

As a Minnesota native, Charlie is experiencing his first summer in Bend. He is in high sprits and can’t wait to swim in the Deschutes.