Strategic Plan
INDIVIDUAL GROWTH. GLOBAL PURPOSE.
At Cheshire Academy, every student is known, challenged, and educated on their own terms. It is a place where faculty are supported to grow in every dimension of their role, and programs are intentionally designed to develop people of character – ready to live purposeful lives as global citizens.
With this in mind and with the guidance of Head of School Tom Woelper P’26, the Cheshire Academy community has undergone a strategic planning process to answer two crucial questions: “Who are we?” and “Where are we going?”
Since early 2025, more than 250 members of our community – students, faculty, staff, alumni, donors, trustees, families and friends – have lent their voices, thoughts, concerns, and praise to this important process. This input led to a refreshed Mission Statement, a solid, forward-thinking foundation for all we do.
Our Strategic Planning Committee then gathered even more input from our community – from ParentPulse surveys to talks with alumni around the globe to ongoing faculty discussions. The goals below are the results of this continuing process.
MISSION
“Cheshire Academy challenges and supports individual students in developing the character, critical thinking, and confidence to flourish as purposeful global citizens.”
STRATEGIC PLAN TIMELINE
our two non negotiableS
The following two statements must be true of Cheshire Academy at the end of the strategic planning process and beyond.
Cheshire Academy will secure and sustain a level of financial health sufficient to serve current students and generations to come.
Cheshire Academy will distinguish itself as the school for a high-caliber, multi-faceted education where expert faculty guide students’ ownership of their personalized pathway to becoming purposeful citizens of the world.
Five Critical Ingredients
Strategic Enrollment: Right Students, Right Mix, Right Size
Attracting, Growing, and Retaining Outstanding Faculty and Staff
Developing Distinctive Programs That Define a CA Education
Renewing Campus Facilities to Catalyze Our Programs
Mobilizing the Resources to Realize the Plan
diVE IN
Cheshire Academy Strategic Plan
Download and peruse the full plan to learn more.
In Conclusion
This strategic plan reflects our community’s beliefs about Cheshire Academy — what it is, what it aspires to become, and what it commits to in the next chapter. At its core, the plan is built around a simple structure: two Non-Negotiables that define what we must accomplish, five Critical Ingredients that explain how we will achieve them, and shared language and definitions that ensure everyone works toward the same vision. Here is that structure in full: the foundation for Cheshire Academy’s next chapter. This plan was led by the Head of School and shaped by every voice that contributed. It belongs to all of us.
Questions? Comments? Want to get involved?
Contact Tom Woelper, Head of School | 203-439-7234 | tom.woelper@cheshireacademy.org
