Head of School
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Meet Dr. Chapman
Head of School
Dr. Dennis G. Chapman, Ed.D.
More than two decades of independent school leadership, grounded in experience, relationships and purpose.
Meet Dr. Chapman
Experienced leadership for Seacrest’s next chapter
Dr. Dennis G. Chapman brings more than two decades of independent school leadership experience to Seacrest Country Day School, including 12 years serving as a Head of School. His career has been distinguished by a record of strengthening schools academically, financially and organizationally while building connected communities centered on students, faculty and mission.
20+
Years in independent school leadership
12
Years serving as a Head of School
Ed.D.
Educational Leadership, University of Pennsylvania
FCIS
Board of Directors & Accreditation Commission
Leadership Experience
A career of institutional growth
The Village School of Naples
Head of School
- Enrollment increased by more than 60%
- Faculty retention reached 97%
- Annual fundraising grew to approximately $2 million
- Led strategic planning, campus planning and FCIS accreditation
- Three-time Platinum AP Honor Roll School
The New School
President & Head of School
- Launched an Upper School
- Developed a $62 million campus master plan
- Oversaw $30 million in construction and renovations
- Raised $15 million during his tenure
- Enrollment grew by 30%
The Out-of-Door Academy
Associate Head of School for Advancement
- Raised $30 million during his tenure
- Led a successful $15 million capital campaign
- Helped grow endowment from $200,000 to more than $12 million
- Oversaw award-winning marketing and communications
Education
University of Pennsylvania
Doctor of Education in Educational Leadership
Doctoral research: Servant Leadership and Teacher Retention in Independent Schools: Examining the Role of the Head of School
University of South Florida
Master of Education in Educational Leadership,
concentration in Nonpublic School Leadership
Trinity International University
Bachelor of Arts in Mass Communications,
minor in Marketing
Independent School Leadership
Dr. Chapman serves on the Board of Directors of the Florida Council of Independent Schools (FCIS) and its Accreditation Commission.
He has chaired multiple school accreditation teams and has presented at national and regional conferences, including the National Association of Independent Schools and FCIS.
His leadership experience spans strategic planning, academics, governance, accreditation, enrollment, advancement, finance, campus development, faculty development, athletics, arts and community engagement.
Read Dr. Chapman’s Full Bio
Dr. Dennis G. Chapman brings more than two decades of independent school leadership experience to Seacrest Country Day School, including 12 years serving as a Head of School. His career has been distinguished by a record of strengthening schools academically, financially, and organizationally while building connected communities centered on students, faculty, and mission.
Before joining Seacrest, Dr. Chapman served for eight years as Head of School at The Village School of Naples. Under his leadership, the school experienced significant institutional growth: enrollment increased by more than 60 percent, the Upper School expanded substantially, faculty retention reached 97 percent, and the school earned recognition as a three-time Platinum AP Honor Roll School. He also led strategic and campus master planning, FCIS accreditation, academic and curricular expansion, and significant investments in faculty development and student support.
Dr. Chapman’s leadership has also produced significant advancement and financial results. At The Village School, annual fundraising grew from approximately $200,000 to $2 million, a $2 million endowment was established, and a $3 million capital campaign was completed in three months to support campus and program improvements. During the same period, the school’s operating budget grew from $6 million to $18 million, including a turnaround from a $750,000 annual deficit to an operating reserve in one year.
His experience leading independent schools extends well beyond Naples. As President and Head of School at The New School in Fayetteville, Arkansas, Dr. Chapman launched an Upper School, led strategic planning, developed a four-phase $62 million campus master plan, and oversaw $30 million in construction and renovation projects. He launched a $25 million capital campaign, personally secured lead gifts of $10 million and $3 million, and raised $15 million during his four-year tenure. Enrollment grew by 30 percent during that period.
Earlier in his career, Dr. Chapman spent more than seven years at The Out-of-Door Academy in Sarasota, ultimately serving as Associate Head of School for Advancement. There, he raised $30 million, led a successful $15 million capital campaign, helped grow the school’s endowment from $200,000 to more than $12 million, and oversaw an award-winning marketing and communications strategy that contributed to a 200 percent increase in applications. His leadership responsibilities also included Board governance, strategic planning, admissions and retention, professional development, communications, and auxiliary programs.
Across these leadership roles, Dr. Chapman has guided schools through accreditation, strategic planning, enrollment growth, academic innovation, campus expansion, fundraising, financial stewardship, governance, faculty development, athletics, arts, and community engagement. This breadth of experience gives him a comprehensive understanding of the opportunities and responsibilities involved in leading a mission-driven, PK–12 independent school.
Dr. Chapman earned his Doctor of Education in Educational Leadership from the University of Pennsylvania. His doctoral research focused on Servant Leadership and Teacher Retention in Independent Schools: Examining the Role of the Head of School. He also holds a Master of Education in Educational Leadership with a concentration in Nonpublic School Leadership from the University of South Florida and a Bachelor of Arts in Mass Communications with a minor in Marketing from Trinity International University.
A respected leader within the independent school community, Dr. Chapman serves on the Board of Directors of the Florida Council of Independent Schools (FCIS) and its Accreditation Commission and has chaired multiple school accreditation teams. He has presented at national and regional conferences, including the National Association of Independent Schools and FCIS, on topics ranging from servant leadership and faculty retention to admissions, communications, and school leadership.
At the heart of Dr. Chapman’s leadership philosophy is servant leadership: listening carefully, investing in people, strengthening community, and creating the conditions in which students and educators can thrive. As Head of School at Seacrest, he brings both a deep understanding of independent education and a demonstrated ability to translate vision into sustainable institutional growth.
Educational Philosophy
Preparing students to shape what comes next
“I believe the best education does more than prepare students for the next grade, the next course, or even college. It develops curious, confident young people who know how to think, collaborate, communicate, adapt and continue learning throughout their lives.”
Cultivating a Love of Learning
Great education begins with relationships. When students know their teachers believe in them, they become more willing to ask questions, explore new ideas and discover what excites them.
Creating the Freedom to Try
Learning requires the freedom to make mistakes. Students should be encouraged to experiment, ask difficult questions and stretch beyond what they already know how to do.
Preparing Students for a Changing World
In an age of AI, students need creativity, collaboration, critical thinking, communication, character, ethical judgment and the ability to evaluate and use information responsibly.
Leading Through Collaboration
Meaningful school improvement happens with educators, not to them. Strong schools are built through communication, collaboration, trust and shared investment in the mission.
Read Dr. Chapman’s Full Educational Philosophy
I believe the best education does more than prepare students for the next grade, the next course, or even college. It develops curious, confident young people who know how to think, collaborate, communicate, adapt, and continue learning throughout their lives.
My educational philosophy is grounded in three principles: cultivating a lifelong love of learning, creating an environment where students feel safe to take intellectual risks and learn from mistakes, and continually evolving teaching and learning to prepare students for the world they will inherit.
Cultivating a Love of Learning
Great education begins with relationships.
Some of the educators who had the greatest influence on my own life were not simply those who knew their subjects well. They were the teachers who made learning engaging, recognized potential in me that I had not yet recognized in myself, and made it clear that they genuinely cared about my success.
I believe every student deserves that experience.
When students know that their teachers believe in them, they become more willing to ask questions, explore new ideas, challenge themselves, and discover what excites them. Education becomes more than the acquisition of knowledge; it becomes the beginning of a lifelong desire to learn.
Creating the Freedom to Try
Learning also requires the freedom to make mistakes.
Students should be challenged to stretch beyond what they already know how to do—to experiment, ask difficult questions, test ideas, and sometimes get things wrong. Mistakes are not failures of learning. Often, they are where the most meaningful learning begins.
The same should be true for educators. Strong schools create cultures in which talented teachers are encouraged to innovate, collaborate, and explore new approaches while remaining grounded in sound educational practice.
By combining strong foundational teaching with inquiry, active participation, and thoughtful innovation, we create classrooms where students develop both knowledge and the confidence to use it.
Preparing Students for a Changing World
What students need from their education is changing rapidly.
Information that once had to be found is now available almost instantly. Artificial intelligence is accelerating that change and reshaping how people learn, work, communicate, and solve problems. That makes the role of an exceptional teacher more important, not less.
Our responsibility is no longer simply to give students information. We must teach them how to evaluate it, question it, apply it responsibly, and use it to create something meaningful.
Creativity, collaboration, critical thinking, communication, and character remain essential. In an age of AI, so do discernment, ethical judgment, adaptability, and AI literacy.
Preparing students for the future therefore requires us to continually examine how we teach. We should preserve what is proven and valuable while having the courage to evolve when the world our students are preparing to enter evolves.
Leading Through Collaboration
I believe meaningful school improvement happens with educators, not to them.
As Head of School, I have a responsibility to provide educational leadership, ask important questions, and help establish a clear vision for teaching and learning. But the strongest ideas emerge when faculty and administrators are engaged in shaping that vision together.
Open communication, collaboration, and trust create stronger decisions and stronger schools. When people have a meaningful voice in developing an idea, they become invested partners in making it successful.
That same spirit of partnership should extend throughout a school community—to students, families, trustees, alumni, and others who care deeply about its mission.
The Goal
Ultimately, I want students to leave school with something that extends far beyond a transcript.
I want them to be curious enough to keep learning, confident enough to try something difficult, resilient enough to learn from mistakes, thoughtful enough to question what they encounter, and grounded enough in character to use their abilities responsibly.
If we can give students that foundation while continuing to evolve how we teach and learn, we are doing more than preparing them for what comes next.
We are preparing them to shape what comes next.
— Dr. Dennis G. Chapman, Ed.D.
Head of School
“I want students to be curious enough to keep learning, confident enough to try something difficult, resilient enough to learn from mistakes, thoughtful enough to question what they encounter, and grounded enough in character to use their abilities responsibly.”
Dr. Dennis G. Chapman, Ed.D.
Head of School
Head of School
Message from the Board Chair
Dear Seacrest Community,
On behalf of the Board of Trustees, I am pleased to share that Dr. Dennis G. Chapman has been appointed as the next Head of School at Seacrest Country Day School.
As part of our commitment to a thoughtful and comprehensive search process, the Board engaged Carney Sandoe & Associates, a nationally recognized firm specializing in independent school leadership searches. While we were fully prepared to conduct a broad national search, a unique and compelling opportunity emerged to engage Dr. Chapman in conversation about this role. Through that process, it became clear that Dr. Chapman is exceptionally well aligned with the needs and aspirations of Seacrest.
Dr. Chapman brings more than 20 years of independent school leadership experience, with a strong record of enrollment growth, program innovation, and community building. In his most recent role, he led significant institutional advancement, including substantial enrollment growth, high faculty retention, expanded academic offerings with national recognition, and meaningful investments in both campus and programs. His leadership also strengthened the school’s financial position through successful fundraising initiatives, capital improvements, and long-term sustainability planning.
Dr. Chapman brings a strong record of educational leadership, a deep commitment to students and faculty, and a clear vision for strengthening both community and program.
Throughout our discussions, Dennis demonstrated a genuine appreciation for what makes Seacrest special—its community, its culture, and its potential. He is eager to partner with our talented faculty and staff, engage meaningfully with our families, and build upon the strong foundation already in place.
We are equally grateful to Dr. Kory Gallagher and Mrs. Tyra Turner for their steady leadership and dedication during this transition period. Their commitment to Seacrest has ensured continued momentum and stability for our community.
Dr. Chapman will begin his tenure on June 1st. In the coming weeks, there will be opportunities for our community to meet and welcome him to Seacrest.
This is an exciting moment for our school. We look forward to the future with optimism and confidence as we continue to strengthen our community and advance our mission together.
Sincerely,
Patricia Garcia III
Chair, Board of Trustees
Official Announcement
Seacrest Country Day School Welcomes Dr. Dennis G. Chapman as Head of School
Seacrest Country Day School is pleased to welcome Dr. Dennis G. Chapman, Ed.D., as Head of School, beginning June 1, 2026.
Dr. Chapman brings more than two decades of independent school experience to Seacrest, including 12 years as a Head of School. Throughout his career, he has led PK–12 independent schools through periods of significant growth and transformation, with experience spanning academic leadership, strategic planning, faculty recruitment and retention, enrollment management, governance, accreditation, advancement, financial stewardship, and campus development.
Most recently, Dr. Chapman served for eight years as Head of School at The Village School of Naples. During his tenure, enrollment grew by more than 60 percent, from 392 to 630 students, while teacher retention reached 97 percent. He led the school's strategic and campus master planning processes, guided FCIS accreditation, expanded academic and student programs, and helped the school earn recognition as a three-time Platinum AP Honor Roll School.
His leadership also contributed to substantial institutional and financial growth. At The Village School, annual fundraising increased from approximately $200,000 to $2 million, a $2 million endowment was established, and a $3 million capital campaign was completed in three months to support campus improvements. During his tenure, the school's operating budget grew from $6 million to $18 million, including a turnaround from a $750,000 annual deficit to an operating reserve in one year.
Dr. Chapman's experience as a Head of School began before his return to Southwest Florida. As President and Head of School at The New School in Fayetteville, Arkansas, he led the launch of an Upper School, developed a four-phase $62 million campus master plan, oversaw $30 million in construction and renovation projects, and raised $15 million during his four-year tenure. Enrollment grew by 30 percent during that period.
Earlier in his career, Dr. Chapman spent more than seven years at The Out-of-Door Academy in Sarasota, ultimately serving as Associate Head of School for Advancement. His responsibilities extended across advancement, governance, strategic planning, enrollment and retention, professional development, communications, and auxiliary programs. During his tenure, he raised $30 million, led a successful $15 million capital campaign, and helped grow the school's endowment from $200,000 to more than $12 million.
Dr. Chapman earned his Doctor of Education in Educational Leadership from the University of Pennsylvania, where his doctoral research examined servant leadership and teacher retention in independent schools and the role of the Head of School. He also holds a Master of Education in Educational Leadership with a concentration in Nonpublic School Leadership from the University of South Florida.
His leadership extends to the broader independent school community. Dr. Chapman serves on the Board of Directors of the Florida Council of Independent Schools (FCIS) and its Accreditation Commission and has chaired multiple school accreditation teams. He has also presented at national and regional independent school conferences, including the National Association of Independent Schools and FCIS.
The Seacrest Board of Trustees approached this leadership transition with care and intention, partnering with nationally recognized independent school search firm Carney, Sandoe & Associates. Through a comprehensive process that included interviews and extensive reference and background review, Dr. Chapman's depth of experience, record of institutional leadership, commitment to servant leadership, and understanding of the Southwest Florida independent school community distinguished him as an exceptional match for Seacrest's next chapter.
As he begins his tenure, Dr. Chapman's first priority will be listening and learning. He plans to engage faculty, staff, students, families, trustees, alumni, and other members of the Seacrest community to understand what they value most about the School and where they see opportunities for its future.
Seacrest also extends its sincere appreciation to Dr. Kory Gallagher and Mrs. Tyra Turner for their leadership and dedication during the transition. Their steady guidance has provided important continuity for students, faculty, staff, and families.
With a strong foundation, an accomplished faculty and staff, and a deeply connected community, Seacrest looks forward to this next chapter of leadership and continued growth.
Frequently Asked Questions
- Why was Dr. Chapman selected as Seacrest's Head of School?
- What experience does Dr. Chapman have as a Head of School?
- What was the process for selecting the new Head of School?
- Why was Dr. Chapman considered qualified to lead Seacrest specifically?
- What is Dr. Chapman's educational background?
- Is Dr. Chapman involved in independent school leadership beyond the schools he has led?
- What is Dr. Chapman’s leadership style?
- What are Dr. Chapman's priorities at Seacrest?
- Does Dr. Chapman's appointment mean major changes are coming to Seacrest?
- How will this transition affect faculty and staff?
- How will this transition affect students and families?
- Does Dr. Chapman have experience with school growth and long-range planning?
- Will there be opportunities to get to know Dr. Chapman?
- Who should questions be directed to?
Why was Dr. Chapman selected as Seacrest's Head of School?
Dr. Chapman was selected because his experience closely aligns with the breadth and complexity of leading a PK–12 independent school and with Seacrest's opportunities for continued growth.
He brings more than 20 years of independent school experience, including 12 years as a Head of School, with demonstrated leadership across academics, faculty recruitment and retention, enrollment, strategic planning, governance, accreditation, advancement, finance, campus development, athletics, arts, and community building.
Just as important, the Board found strong alignment between Dr. Chapman's servant-leadership philosophy and Seacrest's community-centered culture. His career demonstrates an ability to honor what makes a school distinctive while building the people, programs, resources, and institutional strength necessary for its future.
What experience does Dr. Chapman have as a Head of School?
Dr. Chapman has served as a Head of School for 12 years.
Before joining Seacrest, he served for eight years as Head of School at The Village School of Naples. Previously, he spent four years as President and Head of School at The New School, an independent PS–12 school in Fayetteville, Arkansas.
His earlier independent school career also includes more than seven years at The Out-of-Door Academy in Sarasota, where he ultimately served as Associate Head of School for Advancement, and experience at The Benjamin School in North Palm Beach.
Together, these roles have given him experience across independent schools of different sizes, communities, and stages of institutional development.
What was the process for selecting the new Head of School?
The Board of Trustees partnered with Carney, Sandoe & Associates, a nationally recognized firm specializing in independent school leadership searches.
While the Board was prepared to conduct a broad national search, a compelling opportunity emerged to engage Dr. Chapman in conversation about the position. He then participated in a comprehensive evaluation process that included interviews and extensive reference and background review. Through that process, the Board determined that his experience, leadership philosophy, and understanding of independent education were exceptionally well aligned with Seacrest and its future.
Why was Dr. Chapman considered qualified to lead Seacrest specifically?
Seacrest is an Early-Learning through Grade 12 independent school, and the Head of School is responsible for far more than academic administration. The role requires leadership across educational programming, faculty and staff, enrollment, advancement, finance, governance, facilities, community relations, and long-range institutional planning.
Dr. Chapman's career has included significant responsibility in each of these areas. His experience also includes leading the creation and expansion of Upper School programs, overseeing PK–12 campus development, strengthening faculty retention, growing enrollment, leading accreditation and strategic planning, and developing the financial and philanthropic resources necessary to support a school's mission.
That combination of educational and institutional leadership was an important factor in his selection.
What is Dr. Chapman's educational background?
Dr. Chapman earned a Doctor of Education (Ed.D.) in Educational Leadership from the University of Pennsylvania in 2024. His dissertation focused on Servant Leadership and Teacher Retention in Independent Schools: Examining the Role of the Head of School.
He also earned a Master of Education in Educational Leadership, with a concentration in Nonpublic School Leadership, from the University of South Florida and a Bachelor of Arts in Mass Communications with a minor in Marketing from Trinity International University.
Is Dr. Chapman involved in independent school leadership beyond the schools he has led?
Yes. Dr. Chapman serves on the Board of Directors of the Florida Council of Independent Schools (FCIS) and on its Accreditation Commission. He has chaired multiple accreditation teams and has held additional leadership roles within FCIS.
He has also presented at conferences for both FCIS and the National Association of Independent Schools on topics including servant leadership, teacher retention, admissions, communications, and school leadership.
What is Dr. Chapman’s leadership style?
Dr. Chapman describes his approach as servant leadership—a philosophy centered on listening, relationships, trust, and creating the conditions for others to succeed.
This philosophy is also an area of scholarly focus for him. His doctoral research at the University of Pennsylvania examined the relationship between servant leadership and teacher retention in independent schools, specifically through the role of the Head of School.
His approach upon arriving at Seacrest reflects that philosophy: listen first, learn from the community, and use that understanding to help shape the School's future.
What are Dr. Chapman's priorities at Seacrest?
His first priority is to listen and learn.
Dr. Chapman plans to spend significant time engaging with faculty and staff and hearing from parents, students, trustees, alumni, and other members of the Seacrest community. He wants to understand what the community believes must always remain at the heart of Seacrest, as well as where opportunities exist to strengthen the School.
Those conversations will help inform future priorities rather than beginning his tenure with predetermined changes. This listening approach is also reflected in his current welcome message to the community.
Does Dr. Chapman's appointment mean major changes are coming to Seacrest?
Dr. Chapman's appointment represents a new chapter in leadership, not a departure from Seacrest's mission or identity.
There are no immediate changes to faculty and staff roles or the day-to-day student experience associated with the transition. His initial focus is on understanding Seacrest—its people, programs, traditions, strengths, and opportunities—before determining future priorities.
The goal is not to make Seacrest into another school. It is to build upon the qualities that make Seacrest distinctly Seacrest while positioning the School for continued strength and success.
How will this transition affect faculty and staff?
Continuity, communication, and relationship-building will be priorities during the transition.
Dr. Chapman's professional and academic work demonstrates a particular interest in faculty culture and retention. At The Village School, teacher retention reached 97 percent in 2025–26, and his doctoral research specifically examined teacher retention and the role school leadership plays in creating healthy independent school cultures.
He plans to meet individually with faculty and staff as part of his effort to understand their experiences, perspectives, and hopes for Seacrest.
How will this transition affect students and families?
Students and families should expect continuity in Seacrest's educational experience and commitment to its mission.
Dr. Chapman's initial focus will be on becoming part of the community—spending time on campus, getting to know students and families, listening to faculty, and learning the traditions and experiences that define Seacrest.
Over time, that community input will help inform opportunities to strengthen programs and the student experience.
Does Dr. Chapman have experience with school growth and long-range planning?
Yes. Long-range planning and sustainable institutional growth have been significant parts of his previous leadership roles.
At The Village School, he led strategic planning and campus master planning while enrollment increased by more than 60 percent. At The New School, he developed a four-phase, $62 million campus master plan and oversaw $30 million in construction and renovation projects.
His experience also includes significant work in advancement, endowment growth, financial planning, governance, and enrollment management—all important components of long-term independent school sustainability.
Will there be opportunities to get to know Dr. Chapman?
Yes. Building relationships across the Seacrest community is one of Dr. Chapman's first priorities.
Families, students, faculty, staff, alumni, and other members of the community will have opportunities to engage with him throughout the school year. His goal is not simply to introduce himself, but to listen and learn from the people who know and care about Seacrest.
Who should questions be directed to?
Members of the Seacrest community are always encouraged to connect with School leadership. Dr. Chapman can be reached at dchapman@seacrest.org, and additional information and opportunities for engagement will continue to be shared with the community.
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