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After over 20 years and nearly an entire career spent at the Aspen School District, Aspen High School Assistant Principal Becky Oliver will leave at the end of the academic year.
Oliver will become the principal at Carbondale Community School in the fall, a kindergarten-eighth grade charter school in the Roaring Fork School District. She is leaving ASD after 17 years at Aspen Elementary School and six years at AHS.
She was first hired at ASD as a special education teacher at the elementary school after spending one year at a school district in New Mexico. At the time, she was the only special education teacher in the elementary school.
Oliver then became a second grade teacher at AES, and in 2019, moved to the high school as an intervention specialist. She assumed the role of assistant principal for the 2020-2021 academic year, filling AHS Principal Sarah Strassburger’s seat once she became principal and former AHS Principal Tharyn Mulberry became assistant superintendent.
“I never ever would have thought that I would have left an elementary school setting, and then I got up here and I ended up falling in love with these kids,” Oliver said. “And I think it’s fun for me because I’ve been in the district for 23 years. The kids that I have at the high school now are kids that I had in second grade, so I’m getting to still work with the same students and families.”
The relationships Oliver has built with students and families is what has made her time at ASD successful, she said. It is the benefit of working at a small school district in a small community, she added.
“I’ve kind of come to realize that I love, I lead and I serve with my whole heart, that’s who I am, and this community has embraced that kind of educator, that kind of leader, and has allowed me to just really invest in the lives of kids,” she said. “I think when kids feel supported and cared about, they are more available to learn.”
Oliver began her role as an administrator as the school district was entering its first full school year since the COVID-19 pandemic started. Before she assumed the role as assistant principal, she was working with students struggling academically as an intervention specialist at the high school.
The pandemic forced her to figure out a new way of meeting the needs of students, she said.
“That’s, to me, where those relationships became paramount with being able to get families to trust us,” Oliver said. “When we started the next school year remote … that was daunting in the beginning because I’d never done the job before and had no idea what I was doing, but we also were at a time in education where nobody had ever done this before.
“I think the kids were different coming back, and I think it took a lot of work for us to reset expectations in the school about how we, as students at Aspen High School, are going to behave,” Oliver said. “And how we’re going to treat each other, and how we as school staff also needed to handle students with a great deal of empathy and compassion and grace, because they have also endured a really tough time.”
When Strassburger became principal at AHS, she encouraged Oliver to apply for the assistant principal role. Strassburger said Oliver’s work with the high school has been integral for the high school, especially as the district was coming out of the pandemic.
“She has been such an incredible thought partner, and I think she makes all of us better,” Strassburger said. “She approaches every situation with empathy and seeking to understand but also while holding people accountable and having really high expectations.”
Oliver was also integral in the school district’s safety and security upgrades while serving as assistant principal at AHS.
She first attended the National Association of School Resource Officers in 2022, and began working with ASD’s school resource officer Cam Daniel and other district leaders to redevelop the district’s safety protocols. That work led the district to adopt a new internal alert system called Raptor, which makes lockdowns more efficient and allows internal staff to access safety information easier.
Less than a week after Oliver trained district staff in Raptor and new safety protocols, the district was one of several districts across Colorado that were targeted in a series of swatting calls.
Since the swatting incident in early 2023, the district has made significant upgrades to its safety and communication protocols. Oliver joined other district leaders at another NASRO conference and helped develop a vision for the future of safety and prevention at ASD.
“(Oliver) was kind of the primary person that kind of stepped up and made most of this happen,” Daniel said. “I don’t want to leave out all of the hard work and the investments the district has made in school safety and the work that took place to the facilities, but (Oliver) has come to two of the national school safety conferences we go to and she has brought a lot of that stuff back and implemented it as policy and procedure here.”
Oliver wasn’t looking for a new job when the principal position at Carbondale Community School opened, but when she saw the opportunity she knew she had to take it.
She received a bachelor’s degree in elementary education and special education, and before she moved to AHS, she originally applied for the principal position at Aspen Community School. Oliver said she is ready to work with younger students again in a smaller school.
“Again, I lead, I love and I serve with my whole heart. It has been my greatest honor to do that in the Aspen School District for this long, and now I’ve reached a point where I’d like to keep doing that but on a smaller scale,” she said. “I think at this stage in my career, I was really just looking for some better balance in my life and figuring out how I didn’t have to give up who I am and how I want to do things to still impact the world of education in the way I want to. And I think I have a lot left to offer education."
It will allow Oliver to move from an assistant role to a lead role as principal, and give her a chance to work with students in early literacy, one of her favorite parts of teaching elementary school.
Oliver’s last class of second graders that she taught at AES are in eighth grade this year. Though she won’t be able to continue a tradition she had of recreating second grade photos with her students in their caps and gowns on their graduation day, she will still be close to the community and maintain the relationships she made during her 23 years at ASD.
“This really, truly, is my family, and I think that is going to be the hardest thing for me to leave,” Oliver said. “It’s been an honor to care for these people and I’m excited to continue doing that in a new environment.”