Dean and Jeannie Thiessen Retire After Nearly 12 Years at Winston Grocery Outlet
Dean and Jeannie Thiessen have retired after nearly 12 years running Winston Grocery Outlet. Incoming owners Josh and Jelly Wilson offered positions to every employee, while store hours and community traditions continue.
After nearly 12 years of running Winston Grocery Outlet together, Dean and Jeannie Thiessen have retired, closing a chapter that included food drives, community fundraisers, and friendships formed across the checkout counter.

The husband-and-wife team were the store’s original owners and operators when it opened Nov. 20, 2014. Josh and Jelly Wilson are the incoming owners, according to Jeannie.

Every employee was offered a position by the new owners, she said, with each person deciding whether to stay. Store hours remain unchanged at 8 a.m. to 9 p.m.
The Thiessens’ path to Winston began in January 2013, when they started training with Grocery Outlet at stores in the Seattle area, including Skyway and Renton. They were selected for the Winston store in September 2013.
Jeannie said they wanted to leave the corporate world and become independent operators, giving them more freedom to run a business and help people in their community. Winston’s small-town atmosphere helped draw them here.
“What brought us to Winston, is the small town community feel where we can make a difference,” she said.
That goal became part of their work throughout their years at the store. The Thiessens helped replenish the pantries at the Winston Dillard Food Bank and Dillard Church of God and held fundraisers for a variety of local needs.

Their efforts also included an annual peanut butter drive supporting Lunch Box Express, which provides free summer lunches for children in the Winston-Dillard area. In June, The Roseburg Receiver reported that the store’s fifth annual drive collected 453 large jars of peanut butter.
Among their favorite memories were Dream Nights at Wildlife Safari, which Jeannie described as special evenings for terminally ill children. The couple supported the events for years.
Another favorite was Trunk or Treat, organized in partnership with Dillard Church of God. Jeannie said the celebration has grown to draw about 3,000 families each year, becoming one of the traditions they will miss.
Customers can expect that event to continue. This year’s Trunk or Treat is scheduled for Oct. 30 from 6 to 8 p.m. The store’s annual campaign inviting shoppers to round up their purchases for Douglas County Cancer Services also continues through Oct. 31.
Wildlife Safari was part of the store’s story from the beginning. Looking through opening-day photographs, Jeannie recalled that even the safari’s cheetahs came to mark the occasion.

Nearly 12 years later, she said the employees and community are what the couple will miss most. She thanked customers for their generosity and credited the store’s dedicated team of employees as its backbone.
The Thiessens now look forward to reconnecting with family and dear friends in retirement. They also leave the business with lasting connections to the town they chose more than a decade ago.
“We have made so many dear friends in Winston,” Jeannie said.

Congratulations to you both on your retirement! You have been a wonderful asset to our community.
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