News and Opinion from Sisters, Oregon

Cundiff closes out school career

Shirleen Cundiff rolled into Sisters in 1998 with her two daughters, Jamie and Kelly, the day before school started, fulfilling a dream she and her husband, Gary, had kept for many years of residing in Central Oregon. The dream became reality when Gary was offered a managerial job at J and J Carpets in Bend.

“We researched schools in the area and Sisters quickly rose to the top of our list,” she said.

Sisters, with around 800 residents within the city limits at the time, was quite a change from her hometown of Camarillo, California, just north of Los Angeles.

Jamie enrolled at Sisters High School as a freshman while Kelly entered Sisters Middle School, which is where Shirleen’s career with the district first got traction.

“Mary Lesowske asked me if I would ever be interested in subbing in the office and before long I was volunteering and subbing at the district office under superintendent Steve Swisher and human resource manager Jan Martin,” said Cundiff. “I got hired as the receptionist at the district office the following year and became the Human Resource Specialist in 2004.”

Her long career with the district, which also included stints as secretary to the superintendent and homeless liaison, drew to a close on June 30 when her retirement became official.

Looking back over her 21-year career, Cundiff recalls working for six different superintendents, as well as two interims “all of which brought different leadership styles, vision, goals and personalities to the district.”

Her involvement with the Sisters Starry Nights concerts remains a favorite part of her time working and living in the district.

“Being a small part of the Starry Nights Concert Committee continues to be a highlight of my career,” she said. “It brings the spirit of Sisters together to raise money to benefit our schools and for our community to enjoy a high-class concert.”

Cundiff says she worked with a philosophy found in words attributed to Maya Angelou: “People will forget what you said, people will forget what you did, but people will never forget the way you made them feel.”

As the human resource specialist Cundiff was often the first person potential employees had contact with.

“I wanted to make a good impression and it has been satisfying to help people navigate through the challenges of applying, and if they got hired, seeing their careers flourish,” she said.

Her dedication to serving others and the district at large, always with a smile, was appreciated by her colleagues.

Melanie Petterson, assistant to the superintendent, said, “There are many stories of her meeting employees after hours and on the weekends to help them with insurance or other paperwork needs, even coming down to the district office in her pajamas to notarize papers for someone. Her smile and laugh were contagious and brightened everyone’s day.”

Superintendent Curt Scholl said, “Shirleen is a tireless worker who always strives to do her best work for the district. More importantly, she is a great person and deeply cares for all of our employees and this is why she will be deeply missed.”

Dawn Cooper, who has worked alongside Cundiff for 13 years at the district office said, “Shirleen’s kindness, compassion and genuine interest in a person’s well being was evident in how she treated coworkers, staff and FAN clients. She loved her job and performed it with confidence, commitment, and kind-heartedness. She also had an incredible work ethic.”

Cundiff said the current COVID-19 pandemic has presented her with the biggest challenge of her career.

“We are experiencing changes every day as to how we are going to educate our children,” she said. “These are uncharted waters.”

Given the pandemic restrictions, a big retirement send-off was not possible, but a small outdoor gathering did take place Thursday, June 25 outside the district office to allow friends and colleagues to drop by and wish Cundiff well.

When asked about her plans, she said, “I am looking very forward to a true summer break, which has not been possible for many years since so much human resource work takes place during the summer months.”

She hopes to take a road trip in the fall with her husband to visit the Grand Tetons and Yellowstone and to visit her daughter, Jamie, where she lives in Aspen, Colorado.

But that giving spirit and work ethic can’t be quelled as Cundiff is already thinking about how she can contribute in new ways to the community.

“This community has been so good to me that it is important to me to give back,” she said.

“But I do also want to spend more time with my family and friends. My daughter, Kelly, and her husband, Jeff Wilder, live in Redmond, so I will see more of them. I also look forward to hiking the trails with my golden retriever, Grizzly, and I want to learn to fly-fish.

“I would like to thank our staff, School Board and community for the opportunity given to me for the past 21 years,” she said. “I have tried to create an environment for all people to succeed and feel valued. I am so proud to have been a small part of this exceptional school district family. I will miss everyone.”


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