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Founded in 1794

Strategic Alignment Framework


Meeting students where they are and taking them beyond where they imagined possible.


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heshire Academy stands on the shoulders of 220 years of educational history. We have taught significant leaders who have figured prominently in the history of the United States and the world. We did this work in the past by understanding what our students needed and providing an experience that aided them in becoming the best they could be in life.


That mission remains today and requires us to apply the same foresight that enabled our prior success. A dedicated and capable group of faculty and board members spent substantial time looking into the future to determine how we can best continue to meet the needs of our students, today and tomorrow. The result is a Strategic Framework that affirms our values and provides us the means, in the words of Michael Porter, Bishop William Lawrence University Professor at Harvard Business School, to “delineate a territory in which [Cheshire Academy] seeks to be unique.” The Strategic Alignment Framework states that, “Cheshire Academy meets students where they are and takes them beyond where they imagined possible. Every student at Cheshire Academy receives individual attention and guidance from members of a dedicated and capable faculty. Cheshire Academy challenges and supports all of its students to reach further – take a higher level course, try a new sport, sing a solo – while providing structures and supports that enable students to improve. Cheshire Academy is an international community of learning where young people of character from all over the world come together to develop as students, artists, athletes and leaders.” These sensibilities provide the strategic guidance necessary to help us move forward in a changing world to best serve our students.


Arthur Sheriff said it best when he stated:


Our faculty believe[s] absolutely in the value of steady daily application; in regular and thorough accomplishment of small tasks in order that capacity for greater deeds may follow. We believe also that in working with the imponderable factors of human personality, we should adopt a positive rather than negative attitude. We believe as an article of our educational creed that every [student] has deep within ... powers not yet realized; and our first assumption as a matter of course is that these powers may be discovered and developed. We have faith in every [student]; and having that faith we are willing and eager to allow such opportunity as we can for the proper and healthful evolution of each [student’s] spiritual life. We do not believe in rigid molds.


Guided by Sheriff’s sound philosophy, The Strategic Framework Committee has outlined seven goals:

1. Clarify and fortify Cheshire Academy’s unique place among independent schools by leveraging and marketing the signature programs of the Academy.

2. Strengthen and realign the academic program in ways that enhance the educational experience for students and increase the effectiveness of faculty.

3. Enhance the student experience outside the classroom by ensuring the current offerings and experiences promote character development, life skills, and growth of the whole person.

4. Strengthen the sense of community, commitment to shared values, and school pride among students, faculty and staff, and forge stronger relationships with alumni, parents, and the town of Cheshire.

5. Grow and strategically balance the student body by targeting and attracting motivated students wellsuited to flourish and meet their full potential at Cheshire Academy while actively contributing to the life of the Academy.


6. Recruit, reward, and retain diverse and talented faculty members willing to innovate in the classroom, immerse themselves in the Cheshire Academy community, and make a difference in the lives of the students they teach, coach and mentor.

7. Increase financial resources and reduce tuition dependence by expanding annual giving and other philanthropic support for current operations and building an endowment that will become a source of significant operating income in the future.


We now look to implement this strategy and ensure that Cheshire Academy can provide a life-changing experience for our students now and well into the future. This effort, as it has in the past, will require all of us to work together to achieve successful outcomes. The education of an adolescent, much less a group of them, has always achieved positive results when a group of thoughtful and committed adults apply the best of what we know to helping each student learn. We are proud of what we have accomplished and look forward to creating more capable graduates to lead the future. Our Strategic Alignment Framework helps us continue to improve on this good work and build on our long history of success. The following pages provide an overview of nine components of our program that will be addressed in order to accomplish the seven goals of this Framework.


Academic Affairs ☑☑ ☑☑ ☑☑

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Clarify and fortify the Cheshire Academy marketplace position Strengthen and align the academic program with ... Enhance the non-academic experience, including sports, boarding and day student life, Strengthen shared values Balance student enrollment Attract/Retain faculty talent Improve financial resources


Administration & Business

Grow capacity in admission and marketing (Goal 5) ☑☑ Promote core values and realign Eight Pillars (Goal 4) ☑☑ Benchmark best practices (Goal 7) ☑☑ Enhance campus climate/culture (Goal 4) ☑☑ Engage Board of Trustees to enhance fundraising (Goal 7) ☑☑


Admission & Financial Aid

Balance student body mix (Goal 5) ☑☑ Focused, integrated outreach (Goal 5) ☑☑ Targeted financial aid (Goal 1) ☑☑ Build high performing process and team (Goal 5) ☑☑


Advancement & Fundraising Expand Annual Fund Giving, Capital Giving and Endowment Support (Goals 3 & 7) ☑☑Promote Planned Giving (Goals 5 & 7) ☑☑Begin Capital Projects campaign (Goal 3) ☑☑Reinvigorate Cheshire Academy Parents Association (Goal 4) ☑☑


Communications Generate cohesive branding & messaging (Goal 1) ☑☑ Create an integrated marketing approach that brings all aspects of the Academy together in supporting the branding and messaging (Goal 1) ☑☑ Identify target audiences and develop cohesive plans to improve outreach (Goal 5) ☑☑ Redesign the website to better serve the needs of our audience and allow for greater mobile and tablet compatibility (Goals 1 & 5) ☑☑ Create focused publications to promote signature programs and key components of Academy life (Goal 1) ☑☑


Facilities Enhance locations for signature programs (Goal 1) ☑☑ Enhance residential life spaces (Goal 3) ☑☑ Enhance arts and athletics facilities (Goals 1 & 4) ☑☑ Address deferred maintenance (Goal 1) ☑☑


IT, Library & Technology Continue to serve as a leader among educational institutions by innovating our existing Learning Management System(Goal 2) ☑☑ Incorporate 21st century skills into the program as a whole, to include academic and other experiences (Goal 2) ☑☑ Support an enhanced digital media program for students (Goal 1) ☑☑


Roxbury Academic Support Plan for modest growth within the program to increase student coaching abilities (Goal 1) ☑☑ Generate a successful plan for transitioning the leadership of the program (Goal 1) ☑☑ Clarify, focus the program’s marketing to better relate to the target audience (Goal 5) ☑☑


Student Life Strengthen and transform the existing residential program to a more holistic approach (Goal 3) ☑☑ Develop a stronger athletic program strategy (Goal 3) ☑☑ Generate a more focused character, values and service program (Goal 3) ☑☑ Enhance the international student experience (Goal 4) ☑☑



Strategic Alignment Framework