Management Team

Meet the incredible team of management professionals that work hard day to day to make Bennington Properties the successful company it is.  We welcome and value your questions, comments, and feedback about our team.

Meet the Team

Jessica Pritchard, Guest & Owner Services Manager


Guest & Owner Services Manager Jessica Pritchard has been with Bennington Properties since 2013. Jessica brings a Marketing and Public Relations industry background to her job; formerly working as a Publicist for the Seattle International Film Festival and Membership Representative for the Oregon Athletic Clubs.

Jessica grew up in Irrigon, Oregon, located on the Columbia River, just west of Hermiston. She is part of a close knit family and even attended the same high school as her mom. Both sets of her grandparents were married over 67 years, and both grandfathers were in World War II. Jessica grew up next door to grandparents, and in the same town as her current boyfriend of four years.

Learn more about Jessica

Tiffany Smith, Housekeeping Manager


Housekeeping Manager Tiffany Smith has been scheduling and overseeing daily inspections, cleanings, and outside home care for Bennington Properties since 2012. Before joining the team, she worked for another Sunriver-based housekeeping company. Tiffany and her husband have been LaPine residents for a decade.

Tiffany was born and raised in Southern Oregon. Most of her childhood was spent on an Illinois Valley ranch in Selma, Oregon. As a child, she helped tend to the cows, chickens, horses and pigs on the ranch.

Learn more about Tiffany

Kim Balsama, Director of Sales & Marketing


Kim and her husband, Robert, relocated to Central Oregon from Redwood City, California on a whim, during the summer of 2018 and Kim started her position with Bennington Properties shortly thereafter.

She and her husband recently celebrated their 20th wedding anniversary! Kim’s favorite family tradition is sharing spaghetti and meatballs with Robert on Valentine’s Day, “Lady and the Tramp” style (if you’re sensing the start of an Italian-theme, you’re spot on…).

Kim has worked in the hospitality industry for 16 years and has a Culinary Arts degree from Le Cordon Bleu. If you had an hour to spare, Kim would love to teach you how to make fresh pasta. Even though she loves Italian cuisine, don’t dare try to get Kim eating eggplant—it’s her least favorite food!

Learn more about Kim

Pam Pankey, Human Resources Manager


Human Resources Manager Pam Pankey has been with Bennington Properties since 2005. She brings with her 28 years of experience in the property management industry. At her last place of employment, Pam began as a housekeeper and was promoted to reservation manager, and now she handles all staff changes and payroll for Bennington Properties.

Pam was born and raised in the Northern California town of Cloverdale, California, where her family owned and operated a lumber mill. Because Cloverdale is only about an hour from the coast, she liked to dive for Abalone in Fort Bragg.

Learn more about Pam

Robert Bennington, Owner & CEO
(541) 948.0214


Born in Hawaii, Robert Bennington has lived most of his life embodying the Hawaiian, “Aloha Spirit.” The Hawaiian culture can be seen in his upbringing, as well as in the form of one of his many Hawaiian shirts. In 1841, Robert’s great, great, great grandparents immigrated to Hawaii from New England as a part of the large group of Christian missionaries sent to Hawaii between the years of 1820 and 1860.

Although he was born in Hawaii, Robert and his family moved to Oregon when he was just three and a half years old. He has many fond memories of visiting Hawaii, but Robert considers himself a full-blooded Oregonian. As a child, he cultivated a love for skiing and animals. In high school, Robert downhill ski raced on Mount Hood and Mount Bachelor.

Learn more about Robert

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