Dorothy Flebbe retired from Underwriters in Penticton after working there for 52 years. (Monique Tamminga Western News)

Dorothy Flebbe retired from Underwriters in Penticton after working there for 52 years. (Monique Tamminga Western News)

Dot retires after 52 years with the same Penticton insurance company

Dorothy Flebbe worked with 3 generations of Jamiesons and only took 5 sick days

Dorothy, ‘Dot’ Flebbe only took five sick days in her 52-year career with Underwriters on Ellis Street in Penticton.

On Thursday, July 7, Flebbe spent her last day enjoying the company of co-workers and reminiscing on over half a century with the same company and working with three generations of Jamiesons including Neil.

“It’s a happy day and a sad day,” said Flebbe surrounded by flowers, gifts, balloons and retirement posters in her office.

Dot started her career in insurance in her 20s when Underwriters was then called Cumming and Jamieson, working first with Sr. Jaimeson and then Neil Jamieson. Back then they used a typewriter to write up insurance. The typewriter is still used to this day for special reports.

Now Neil’s son works there so Flebbe likes to call it the 3 generations of Jamiesons.

“When it was Cumming Jamieson it was a two-girl office,” said Flebbe. “Underwriters bought it but Cummings and Jamieson were right there. And then Neil came along and we had two generations of Jamiesons.”

“So it’s loyalty to the family,” said Flebbe as to why she’s stayed with the company so long.

Neil got Dot to join in on all his community efforts including the Panthers, the Hockey Hall of Fame and his beloved Penticton Vees.

“He had me selling tickets to games and taking minutes in the meetings,” she said. “It was a lot of fun over the years.”

One day, Neil and Dot were coming out of a Vees game on a particularly icy night and Flebbe slipped, landing right on her face, taking out some teeth and hurting her one side.

“Neil had his hands in his pockets so he couldn’t grab her,” said one of the staff at Underwriters.

Flebbe went to the hospital and had X-rays and was given a sling.

Black and blue, and swollen, sure enough she showed up to work the next day. Everyone told her to go home but she insisted on staying.

“I was writing with my hand in a sling,” she recalled. “The doctor from the hospital calls me up and said ‘we misread the X-rays. You have a broken arm.”

Flebbe collected quite the following of loyal customers over the years who would ask for Dot and catch up while they get their insurance.

So what is she going to do in her retirement?

“I don’t really know! My kids and grandkids are coming to visit so I’m looking forward to that,” she said.

READ MORE: After 56 years of being a Main Street staple in Penticton, jeweller Ralph Oslund retires

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