Investment in Excellence at CDS:
Strengthening Teaching, Learning, and Student Life
At Carrollwood Day School, we are always looking ahead and asking how we can continue to grow as a community of learners. One of the core commitments in our strategic plan is to make CDS the destination school for exceptional educators in the Tampa Bay region. When we invest in our teachers and leaders, we invest directly in the experience of every student who walks into a CDS classroom.
With that goal in mind, we are excited to introduce three new leadership positions for the 2026/2027 school year that will strengthen teaching, learning, innovation, and student life across our PreK–12 programs. Together, these roles represent an Investment in Excellence and will help ensure that CDS continues to lead in academic innovation while supporting the whole child.
As part of this investment, we are especially proud to share that all three roles will be filled by internal candidates who began their careers at CDS in the classroom. At Carrollwood Day School, we believe in investing in our people and creating opportunities for talented educators to grow as leaders within our community. Each new leader brings the perspective of a teacher, a deep understanding of our culture, and a strong commitment to the mission that guides our work every day. Their journeys reflect our belief that when we nurture the potential within our own faculty, we strengthen the entire school.
Please join us in congratulating Justin Kingsley, Jennifer Dosher, and Holly Black as they step into these important leadership roles. Working alongside our divisional teams, they will collaborate to strengthen the student experience across Carrollwood Day School and continue building the vibrant learning community that defines CDS.
Together, these positions represent a meaningful investment in the people and programs that make our school special. By maintaining a presence in the classroom alongside their new responsibilities, Justin and Jennifer will ensure our leadership remains deeply rooted in the daily lives of our students. They also advance our mission to enrich the mind, strengthen the character, and inspire the passions of our community as we prepare our students to better the world. We are grateful for their dedication to CDS and look forward to the impact their leadership will have on our faculty, students, and families.
Justin Kingsley, Director of Technology Innovation
Justin is a well loved and dedicated CDS faculty member, and we are thrilled that he will bring his talents to this new role. With a background in engineering research, computer science, and mathematics instruction, Justin combines technical expertise with a deep understanding of the classroom experience. Over the past decade, he has led professional development initiatives that help educators thoughtfully integrate emerging technologies to enhance student learning. In this role, Justin will partner with faculty across all divisions to explore the meaningful use of educational technology and AI, ensuring that innovation always supports great teaching and deeper student engagement.
Jennifer Dosher, Director of Teaching and Learning
Jennifer's connection to CDS runs deep. Since joining the school in 1996, she has played an important role in our academic journey, including serving as our first Middle Years Programme Coordinator and helping guide CDS through its early IB development. Over the years, she has mentored teachers, led curriculum initiatives, and remained deeply committed to the craft of teaching. In her new role, Jennifer will oversee curriculum design, instructional practices, assessment alignment, and faculty professional growth across the school. Her work will help ensure that our PreK–12 programs remains cohesive, research informed, and rooted in the inquiry based learning that defines an IB education.
Holly Black, Lower School Dean of Students
Holly brings a deep commitment to student advocacy and the development of the whole child. With experience as both a general education and Exceptional Student Education teacher, she has worked with students across elementary grade levels and supported a wide range of learning needs. During her time at CDS, Holly has quickly become known for her collaborative approach, strong relationships with students and families, and her thoughtful leadership within the classroom and beyond. In this new role, Holly will serve as a visible presence in the daily life of the Lower School, supporting student wellness, guiding restorative approaches to student behavior, and partnering closely with faculty and families to cultivate a positive and inclusive school culture.