2026 Administrator of the Year: Kathy Calkins’ Transformational Leadership in Oregon
Three decades after almost walking away from the school bus, studying behavior changed everything for Kathy Calkins. Now, she oversees 181 buses and leads the 225-person team at North Clackamas with intent and purpose.
Kathy Calkins has served as transportation director for North Clackamas School District in Milwaukie, Oregon, since 2019.
Credit:
Brian McGrew/North Clackamas School District
6 min to read
Kathy Calkins, recognized as the 2026 Administrator of the Year, significantly impacts Oregon's educational transport sector.
With three decades of experience, she transformed her career by studying student behavior and school bus management, leading to her current leadership role.
She currently manages 184 buses and a team of 225 people at North Clackamas, demonstrating intentional and purposeful leadership.
*Summarized by AI
When Kathy Calkins became a school bus driver in 1996 at a neighbor's urging, she almost quit shortly after starting. It turns out that managing a bus full of 50 kids is a whole other challenge compared to raising two boys of her own.
Thankfully, Calkins stuck with it, because now three decades later, she’s leading a high-performing team in Oregon, and we can’t imagine a world without her. Her passion, approach, accomplishments, and care for others make her a very deserving recipient of School Bus Fleet’s 53rd annual Administrator of the Year.
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Path to Teaching & Leadership
There’s no doubt that what fuels Calkins most is people, and she wants everyone to feel like they belong.
Before finding her way to transportation, she mentored youth at a lockdown recovery facility. “I saw firsthand how many youth struggled, and I stayed in that difficult field to reach them before the justice system did,” she said.
North Clackamas Transportation at a Glance
Fleet Size: 184 Buses
Transportation Employees: 225
Students Served: 12,000
Schools: 32
Departments: 7 (routing, dispatch, mechanics, office, recruiting, and training)
Fuels Used: Renewable diesel and propane
Vendor Partners: Verizon Connect, REI, ZU̅M
That mission followed her to the school bus. Armed with the reality of what happens when guidance is missing early in life, Calkins committed herself to being an example when students need it most.
Eventually, she learned the theory of Positive Behavior Interventions and Supports (PBIS). Shifting her attitude to focus on students' strengths rather than their mistakes became a game changer. This is when she realized she was in exactly the right place.
Calkins worked her way up from school bus driver to trainer, third-party tester, core instructor, lead trainer, associate director, and now, transportation director at North Clackamas School District (NCSD). Along the way, she took college courses in school bus management and earned NAPT certifications.
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“I loved motivating drivers by sharing the strategies that had transformed my own career, and I couldn't wait to teach others,” she said. “If I can change a driver's heart toward a child on their bus, that is the best possible day.”
These days, Calkins starts each morning by extending well wishes to each department. Her bi-weekly meetings with each team are her favorite “because it’s a quiet time to talk to my staff and build the relationships that are so important to me.”
Face time is important to Calkins. Here, she does one of her near-daily rituals: Waving as buses leave to pick up students at the beginning of their afternoon route.
Credit:
Sam Freshner
The Secret to Strong Relationships
Calkins calls herself “a servant leader with a side of silliness.” She never compromises the supreme mission and makes time for fun when appropriate.
And she has a knack for making people feel heard and valued. Even when fielding parent or community complaints, she lets the district’s values of equity, relationships, integrity, empowerment, and care guide her approach to problem-solving.
Her motto is to always assume positive intentions, to see the good in nearly every situation, and to search for the “why.” For instance, “If we approached investigations with the assumption that the driver is always at fault, we would fail to create a supportive environment,” she said.
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“For me, the solution has always been listening. When emotions rise, it’s natural to become defensive. But that’s when I remind myself: this moment isn’t about me; it’s about them.”
Calkins knows that behavior must always be modeled from the top, so she works hard to approach each day with a smile and the understanding that some days they can’t always be returned.
This compassion is one reason so many people love working for her. One employee shared this: “I left my previous district because I heard Kathy was here. I commuted 40 miles each way just to be part of her team. ... Kathy is the glue that makes it all happen. She helped me see that my career potential was right in front of me.”
“People come first” is another Kathy Calkins motto.
Like a true humble leader, when we asked Calkins what accomplishment she’s most proud of, she refused to take the credit she so clearly deserves. Instead, gave her team a shout out.
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“My success as a director is a direct result of working with individuals who are deeply committed to safety and efficiency,” she said. “I truly couldn't do any of this without them.”
Calkins is also active in the Oregon Pupil Transportation Association (OPTA), where she received the Trainer of the Year award in 2010 and the Ron Bryan award in 2021. She participates in initiatives such as Fill-A-Bus events, reinforcing the department's role as a community partner.
“Through her engagement, Kathy models leadership that strengthens not only her organization, but the profession as a whole,” Freshner said.
Outside of work, Calkins enjoys going on walks with her husband and spending time with her granddaughter, whom she calls the light of her life. She’s active too, doing CrossFit, camping, hiking, whitewater rafting, skydiving, and bungee jumping.
Key Accomplishments
To be good environmental stewards, NCSD recently introduced propane school buses, complete with an on-site fueling station thanks to grant funding for 16 vehicles. The diesels in the fleet were also converted to run on renewable diesel.
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Calkins has also been busy upgrading technology to increase department efficiency. She recently received approval for ZU̅M, a platform that replaces an antiquated program used for the past 22 years. ZU̅M will consolidate all transportation operations into a single hub, improving on-time performance and tracking while allowing parents to monitor students’ locations. Additionally, tablets will be deployed on all buses to support navigation, student behavior reporting, and communication.
To simplify video management, Calkins secured approval to replace existing camera systems with a unified one featuring stop-arm cameras. Previously, videos had to be uploaded using three different players; the new system allows for direct uploads to a secure server. To support this, she also gained approval for Wi-Fi installation at the transportation hub, eliminating the time-consuming task of manually swapping hard drives.
Calkins stands with the department's two associate directors, Cheryl Cosgrove and James Prichard.
Credit:
Kathy Calkins/NCSD
COVID hurt NCSD’s driver pool, with the district forced to do layoffs. Left with 150 staff, Calkins’ first order of business was to hire a full-time transportation recruiter. After four years, they’re fully staffed again. Adding some van drivers who didn’t need a CDL helped, too.
“Since assuming leadership of NCSD transportation, she has rebuilt a struggling department into a fully staffed, high-performing, and nationally competitive operation,” said Sam Freshner, dean of transportation. “Her leadership demonstrates that when people feel supported, valued, and trusted, organizational performance follows.”
What’s Next?
Leadership and personal growth are a journey that never really ends, and Calkins knows that. “My ongoing goal is to be the best version of myself so that my staff can be the best version of themselves,” she said.
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With new software soon on the way, she’s gearing up to navigate the rollout and the change that will come with it. With her approach to it firmly rooted in positivity, support, and teamwork, she’s well-positioned to see even greater fruits of her labor.
What matters most is supporting the people around us, and Calkins never hesitates to credit the work of her entire team for the department’s success. Pictured here is the NCSD Transportation staff for school year 2025-26.
Credit:
Kathy Calkins/NCSD
As for the future of the industry, she hopes to see a few things:
Districts continuing to hire managers who genuinely care for and support their staff.
Drivers who truly care about students and who show them care.
Parents acknowledging that mistakes happen, especially when drivers’ backs are to the children.
A simulator that helps drivers practice real-life challenges, particularly around student behavior, to learn problem-solving on the fly when the stakes are much lower.
As it settles in that she won Administrator of the Year, Calkins said she plans to “continue earning the right to receive this award and to keep the flame burning in the care of my staff, students, parents, and district.”
Calkins will never not be a champion of the people she knows and understands. “I truly believe school bus drivers are world changers,” she shared.
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She is right about that. But what she doesn’t fully realize is that she is also changing the world.
Know an inspiring district or state transportation director you think should win this award next? Nominations for the 2027 SBF Administrator of the Year are now open through Jan. 29, 2027! Send in your nomination here.
Kathy Calkins is the director of transportation at North Clackamas Schools in Oregon, and the recipient of the 2026 School Bus Fleet Administrator of the Year award. She is recognized for her transformational leadership in school transportation.
Three decades ago, Kathy Calkins almost left the school transportation sector, but studying behavior transformed her approach and career trajectory once she understood why children do what they do and how adults can better communicate and interact with them.
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