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

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

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.

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Shannon Gleasman, Reservation Sales Manager, Real Estate Broker
(541) 326.2184

As a native Oregonian, graduate of the University of Oregon and 4th generation broker, Shannon has a genuine passion for this area and the people here. While a desire for new experiences and connections brought her around the world; a Rotary Youth Exchange in Denmark, semester abroad in Chile and travel with her husband in Central America, there is no place quite like home. Shannon's love of the mountains and priority to be near family made the move to Central Oregon in 2011 a perfect fit. Her background in hospitality services across Oregon and experience in client relationships, revenue management and marketing of vacation homes gained through Bennington Properties gives her an in-depth knowledge of Sunriver and the vacation rental home market. Shannon's heartfelt approach to her interactions with each individual ensures you will experience personalized care and attention to detail when buying, selling, or renting your home.

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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.

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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

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