Brooke Gregory has a strong competitive streak, one that's served her well during her 23 years in the Cherry Creek School District.
Since she took her first job as an English and social studies teacher at Prairie Middle School in 1993, Gregory has been intent on being the best. It's a focus that's persisted over the years, as Gregory has held a wide array of posts across the district. In her roles as teacher, dean, principal, administrator and, in her current post as Assistant Superintendent of Educational Operations, Gregory has worked hard to excel.
Happily, it's an attitude that's fit seamlessly with the general philosophy of the Cherry Creek School District.
"When I got here, I felt like folks were committed to the mentality of being the best and making our students proud of where they went to school and proud of the education they got," Gregory said. "As someone who is competitive, I like the challenge of wanting to be the best. It's something I'll chase my entire career, but I'm glad that I work in an organization that doesn't settle."
For Gregory, that attitude has had different meanings and applications with different job titles. But the end result of her competitive nature has never been selfish. In her myriad roles in Cherry Creek Schools, Gregory has always been focused on students. Her push to excel has always been tied directly to the benefit of thousands of kids and the wider Cherry Creek School District community.
It's an investment that hasn't come in a vacuum. Since she reported to her first job in the district, Gregory has seen her son progress through Cherry Creek schools and return as a new teacher. She's built a broad network of personal connections across the district's 108 square miles, and those ties have made her work all the more engaging and important.
"The blurred lines between my professional and personal life have made my work here a bigger experience for me," Gregory said. "It's one thing to send my son to school here, but over time people from many different parts of my life had kids in our schools. My network of life became intertwined with Cherry Creek Schools."
Her engagement and investment in the people of the district have helped steer her somewhat nontraditional path through the district. Gregory found a rapid route to an administrative position after her initial years at Prairie as a teacher and dean and a short stint at the newly opened Falcon Creek Middle School. She accepted the position of director of the district's Office of Multicultural Services and Student Success, a role that took Gregory from a single building to district-wide responsibilities and saw her doing important equity work for students and teachers across Cherry Creek.
"I feel like the beauty of my career is that I’ve loved every job I’ve
had. I always knew how I could contribute ... I still see being in
this district as such an amazing opportunity … There’s no place in this
district you could put me and I wouldn’t be happy."
-- Brooke Gregory, Assistant Superintendent of Educational Operations
But the distance from the classroom and from her roots as a teacher was too far. After six years, she wanted to be back among students, teachers and community members, and she headed to Cherokee Trail High School to serve as assistant principal and ultimately principal, a time she remembers as among her favorite in the district. While she eventually headed back to administrative positions as Executive Director of High Schools and Assistant Superintendent of Human Resources, her focus never strayed from the people who give the district its purpose.
That's part of the reason her current post as Assistant Superintendent of Educational Operations is such a good fit for Gregory. The position offers the best of both worlds.
"If I'm not going to be directly involved with students and teachers and families every day, this is about as close as I can get. I'm in a central administration role, but I still get the flavor of those aspects of relating to the firsthand experience," she said. "I feel more tied to kids and teachers in this role. I like that."
Gregory's pursuit of excellence is tied to people, and it's no wonder. As a third-generation educator, Gregory is pursuing a family legacy. As the first African American woman to serve as an assistant superintendent and member of the District Leadership Team in the Cherry Creek School District, she's worked hard to ensure that the district's commitment to excellence and academic achievement applies to every member of its diverse community. And as the mother of a CCSD alum and a current classroom teacher, she's discovered a different kind of perspective on the hard work that goes into education.
"I miss being in the classroom every day, but I feel like the beauty of my career is that I've loved every job I've had. I always knew how I could contribute," Gregory said. "I still see being in this district as such an amazing opportunity … There's no place in this district you could put me and I wouldn't be happy," she said, adding with a laugh, "If we continue to have a shortage of bus drivers, I'd be happy to start my day driving, because I'd be with the kids."