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Cassidy Webb

Rosheika Rolle Named 2024 Assistant Principal of the Year


Individuals who work in education make a significant impact on the community, providing the foundation for kids to thrive and reach their full potential in life. Rosheika Rolle, who serves as Assistant Principal at James S. Rickards Middle School, stands out among the dedicated educators in the Oakland Park community. She was recently named the 2024 Assistant Principal of the Year by Broward County Public Schools.

A Glimpse Inside Rolle’s Journey in the Education Field

Rolle always knew she wanted to be a teacher due to her love of children. Her father was a teacher and principal in the Bahamas, and coming from a background of educators and leaders, her passion for education was deeply rooted.

After obtaining two masters degrees in educational fields, she got into the industry of education in 2006 at Rock Island Elementary School where she had volunteered in the past. She started as a third-grade teacher, spent a few years teaching fifth grade, then made the transition to Lauderdale Lakes Middle School.

“Everyone is afraid of middle school but I love it and wouldn’t change it for the world,” Rolle explains. While she enjoys a love of teaching, she also aspired to be a leader and wanted to impact lives on a larger scale. After completing the Principal Prep Program, she became a magnet coordinator where she got to promote the school’s exemplary magnet program. Then, in 2016, she was promoted to assistant principal, during which time she was able to assist in moving the school from being a three-time D school to a C school.

Her experience led her to James S. Rickards in 2021.

Rolle’s Impact on James S. Rickards Middle School

Ms. Rolle transitioned to Rickards at a tumultuous time. After a devastating partial roof collapse in 2021, students and faculty were faced with the challenge of learning in portable classrooms.

Rolle was put in charge of overseeing much of the construction, meanwhile, she led the reunification of three campuses. This experience taught her how to lead through adversity and how to embrace change.

Reflecting on the obstacles that she helped the school navigate, Rolle says “We must continue teaching the kids whether in a building or at a park…I think the transition [to Rickards] was the best move ever. I’m meant to be here.”

Fostering a Supportive and Inclusive Environment for Learning

Rolle’s experience at Rickards has been driven by her commitment to maintaining close relationships with staff, teachers, and students. “It’s all about relationships,” she says. She prioritizes creating a positive and supportive environment where everyone feels valued.

With a large population of students for whom English is not their first language, it is especially important to her to make sure students feel as though they are part of the community. “A lot of my students speak Spanish, and I laugh and say, ‘I speak Spanglish,’ because I understand more than I speak.” Despite the language barrier, Rolle is able to develop deep connections with her students, and they appreciate that she tries to communicate with them.

Rolle mentions that it is important to check up on teachers, too. “They are human, and it’s not all work all the time. You have to ask people how they are doing and see people for who they really are.”

Her dedication to providing a positive and supportive environment undoubtedly plays a crucial role in shaping the success Rickards has seen in recent years.

Lessons Learned

A popular saying in education is that “all children can learn.” Although she had heard that before, working at Rickards has demonstrated to her that it is true. She explains, “All children can learn, but it is up to us [educators] to find a way in which they can learn and make sure they are receiving the support they need.” She believes all children can learn no matter what background, language barriers, or disability.

Looking Forward to the Future

As she looks to the future, Ms. Rolle’s vision for James S. Rickards Middle School is clear: help more students and impact more lives. She plans to make sure they are on track with everything that is needed for the new building while continuing to show the community that her students can and do make progress.

The new building, which broke ground in November 2023 will feature a coding program, a media center, new science labs, and much more. Rolle wants the community to know that “Rickards is here to stay. We are here to serve and we’re not going anywhere!”


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