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Meet the Cabinet: Chief of Strategic Initiatives Brooke Gregory

​Welcome to "Meet the Cabinet," a series of stories and videos focused on members of the Cherry Creek School District administration. This series is designed to highlight the work and experiences of those who help steer the direction, vision and everyday operations of Cherry Creek Schools.

CCSD Chief of Strategic Initiatives Brooke Gregory.Brooke Gregory sees a sense of future direction in the Cherry Creek School District's long-held values.

For Gregory, the district's Chief of Strategic Initiatives, the mission statement "Dedicated to Excellence" is more than a summation of Cherry Creek Schools' past approach to the task of educating thousands of students. It's also a key to success for the future, a straightforward guidepost that can effectively lead the district's current Cabinet through the tests of years to come.

"As things come and as things test us and as things push us, let's really use those words as a filter to say, 'We know who we want to be. Let's stick to those core values,'" Gregory said. "That's the standard that we're going to hold ourselves to. Nobody has to impose that on us."

Over nearly 25 years in the district, Gregory has worked hard to translate Cherry Creek Schools' mission statement into a practical reality that benefits students, teachers, staff and community members alike. Since she took her first job as an English and social studies teacher at Prairie Middle School in 1993, Gregory has been intent on realizing the district's goals. It's a focus that's persisted over the years, as Gregory has held a wide array of posts across the district. In her past roles as teacher, dean, principal, administrator and, in her current post as Assistant Superintendent of Educational Operations, Gregory has worked hard to excel and stay true to the district's values.

In her current position as Chief of Strategic Initiatives, she's working hard to ensure that visions translate into real, measurable progress. Gregory worked with Superintendent Scott Siegfried to create her current position, which focuses on making sure that the goals set out by district administrators are being met by those in the individual school buildings and classrooms.

"The exciting part of this position is that it's really about supporting our schools and our departments to make sure that we do the things we say we're going to do at the highest possible level," Gregory said. "We want to provide measurable outcomes and evidence of our progress as we go."

Gregory's new position comes at a critical time for Cherry Creek Schools, as the entire district has ramped up its focus on innovation and 21st-century skills. From new innovation spaces in every CCSD elementary and middle school to the construction of the new Cherry Creek Innovation Campus, focused on further expanding options for high school students studying career, technical and professional fields, the district is working hard to prepare all students with the proper skills for the academic and professional demands of the future. Along with the district's continuing work in equity for students, professional development for staff and other important goals, these new steps pose many challenges.

All of these lofty ambitions have to translate to measurable gains, and that's where Gregory's work comes in.

The work making sure that the there's a clear connection between goals and results doesn't come in a vacuum for Gregory. 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.


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. 

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, her focus never strayed from the people who give the district its purpose.

That's part of the reason her current post 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 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."

Posted 10/23/2018 2:13 PM

"The exciting part of this position is that it's really about supporting our schools and our departments to make sure that we do the things we say we're going to do at the highest possible level ...We want to provide measurable outcomes and evidence of our progress as we go."

Brooke Gregory, Chief of Strategic Initiatives, Cherry Creek School District 

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