Founded in 1926, Wooster School, a co-educational, K-12, college preparatory day school, is located in Danbury, Connecticut. Wooster School stands on a firm foundation of teaching, learning, and community values. While our strong community traditions of self‐help and relationship building have long been recognized as strengths, our more recent commitment to innovative approaches to thinking, skill‐building, and the development of dispositions have the potential to push us into position as a regional school of choice for families who recognize that learning how to think, to learn, and to create relationships will be key to the success and fulfillment of our students in the 21st Century and beyond. We are a school of thinkers, learners, and creators. By combining tradition, innovation, and the power of relationships, Wooster produces curious, capable and compassionate young people with the skills and dispositions to be successful and fulfilled in college, and in life.

Chief Financial Officer

Deerfield Associates has been retained by Wooster School, located in Danbury, Connecticut, to conduct a national search for a Chief Financial Officer. Wooster School, founded in 1926 by Rev. Dr. Aaron C. Coburn is located in Danbury, Connecticut. The Head of School is Matt Byrnes. The religious affiliation is Episcopalian heritage, although Wooster serves students from many faiths and religious traditions. The School is located on a scenic 127 acre campus with 15 buildings. Wooster School is primarily a day school though there are some boarders who live with host families in the area. The annual operating budget is $10.4 million dollars. Enrollment is comprised of 366 boys and girls in grades K – 12. Lower School (K-5): 60, Middle School (6-8): 101, Upper School (9-12): 205. Twenty (20) Connecticut towns and twenty-two (22) New York State towns are represented. Number of full-time faculty: 54; number of full-time faculty with advanced degrees: (95%). In Lower School (K through Grade 5), the individual class size ranges from 8-16, with an average of 11 students per class. In Middle and Upper School, a faculty member typically teaches 4-5 sections per day, and the class size ranges from 4-18 students, with an average of 12 students per class. For more background on Wooster School please visit www.woosterschool.org.

Wooster School seeks a strategically-oriented and experienced financial and business leader to fill the key position of Chief Financial Officer. This opportunity is available in July 2019. The CFO will work closely with the Head of School in support of the school’s mission and strategic plan. The CFO is responsible for the organization, management and implementation of comprehensive business, financial, facilities and investment initiatives for the school. The new CFO will be a key member of the senior leadership team that oversees the day-to-day operation of the school as well as the “big picture” issues and ambitious plans that outline the school’s future. The ideal candidate for this high-profile position is a strategic thinker who has exceptional leadership and critical thinking skills. Our goal is to recruit a seasoned professional who will build on the significant accomplishments of the outgoing CFO (who is retiring in July 2019) and determine what policies, technologies and programs need to be adapted to respond to the needs of the school and its strategic priorities. The candidate will be proficient with accounting systems and in effective data management and analysis to support innovation and efficiency across the organization. For a full search description of the opportunity, responsibilities and academic and business credentials required please view: https://deerfieldassociates.com/wooster-school/

Wooster School offers a dynamic and supportive work environment, competitive salaries and a generous benefits package including a retirement plan, paid vacations, and medical insurance. Wooster School is an Equal Opportunity Employer.

To explore this superb career opportunity on a highly confidential basis please send your resume, letter of interest and list of references (who will be contacted only if mutual interest is determined) to: Doug Cooney, Executive Search Consultant, Deerfield Associates Executive Search, Inc., 572 Washington Street, Suite 15, Wellesley, MA 02482 Telephone: 781-237-2800. Email: jobs@deerfieldassociates.com

Humanities Teacher

Wooster School is looking for an experienced English teacher with a strong background in writing and the Humanities who is interested in joining a 9th and 10th Grade Humanities team as a collaborative co-teacher. The ideal candidate will have an advanced degree and/or teaching experience in English and a deep understanding of process in writing. Candidates should also be voracious readers and seekers of new knowledge with a deep desire to foster that same disposition in our students. Experience as a teacher of writing at the secondary or postsecondary level is a plus. Applicants should be familiar with the workshop model of reading and writing. Applicants should also be curious, innovative students of the art and science of teaching and learning, as collaboration and professional learning are core elements of the Wooster learning community.

The skills of reading for understanding from different forms of primary sources, literature and nonfiction texts, and making meaning from those texts, is one primary goal of the program. Another is that students develop advanced writing skills and can employ them in the service of problem identification, reflection, and effective communication of ideas. Advanced writing skills are built from the ground up, starting with a firm understanding of the writing process and how sentence structure, organization, and style contribute to that process.

As a Wooster teacher, the ideal candidate will be comfortable creating and collaborating with the teaching team on effective writing workshop experiences and providing intentional, effective individualized feedback to developing writers.


  • Believe deeply in the mission, beliefs and values of Wooster and subscribe to Wooster’s culture of thinking and learning.
  • Co-teach the Humanities course with a history teacher.
  • Plan and implement lessons based on the Wooster School Writing model.
  • Hold high expectations for every student.
  • Provide necessary accommodations and modifications for the growth and success of all students.
  • Plan, structure, and share lessons that are engaging, that make our students think every day, and that are aligned with a year-long scope and sequence.
  • Work as an active, collaborative member of the learning group, grade-level, content area and school-wide teams,to ensure our students’ needs are met.
  • Keep students and parents well informed of student progress by providing regular feedback, focused learning intentions and clear success criteria.
  • Participate in school-wide professional development beginning in August.
  • Seek continual feedback and coaching to develop as a teacher learner.
  • Be available and committed to ongoing verbal dialogue and conversations with the parents and the Wooster community.
  • Perform necessary duties including, but not limited to, advisory, after school activities and chaperoning.


  • Strength in writing content area.
  • A bachelor’s degree or higher and mastery of core subject: writing.
  • At least 3 years of successful teaching experience.
  • Excellent written and oral communication skills.
  • Teacher certification preferred.

Salary & Benefits

This is a full‐time, exempt position. Salaries are competitive with the local independent schools. Competitive benefits package includes health coverage.

To Apply

Interested candidates should submit a cover letter, resume, and statement of philosophy to:

Elizabeth Higgins
Director of Teacher Learning

Assistant Ice Hockey Coach

The Assistant Ice Hockey Coach assists in all aspects of team development; including coaching, motivating, mentoring, and the recruitment of families.

Education/Skills Requirements

An Associates Degree is required; Bachelor’s degree is strongly preferred. Required skills include: Knowledge of ice hockey skills and strategy and the ability to effectively teach them; ability to motivate and effectively communicate with young student-athletes; willingness and ability to actively recruit qualified candidates to Wooster School; commitment to being a positive member of the Athletics Department, the Wooster School community, and the ability to influence his/her athletes to do the same.

Administrative skills such as prioritization and organization are needed. The coach must be self-directed and motivated and be able to work collaboratively. Current CPR and First Aid certification must be on file.

Experience Requirements and/or Equivalents

Significant experience playing and coaching boys or girls hockey, as a player at the college level, or as a coach at the club or secondary level or above, is strongly preferred. Salary is commensurate with experience.


Coaches are expected to be on present during the hockey season (mid-November – early March) during all practice (6:00 am or 3:15 pm) three days per week and game times (between the hours of 3:30 pm and 7:00 pm Monday - Saturday). Games are consistently held on a Wednesday, Friday, and Saturday. Occasionally it is requested by the Administration or the Athletic Department that you attend various school events, these are advised and at times required.

Additional Information

Please apply online to Jeff Carone, Athletic Coordinator at jeff.carone@woosterschool.org with a resume, and 2 references no later than October 19, 2018. Salary is commensurate with experience. Employment in this position is contingent upon the successful completion of all required pre-employment background checks. Wooster School is proud to be an equal opportunity employer that encourages diversity in the workplace.

Tutor for Specialized Therapies

Specialized therapy tutors support our K-12 students with language based learning differences by providing interventions and remediation while working with parents, teachers, and outside professionals on best practices. Specialized therapy tutors should have training and experience using the Orton Gillingham method and programs like the Wilson Reading System and the Just Words Program. In addition, tutors should be well versed in teaching comprehension strategies, specifically using Lindamood Bell’s Visualizing and Verbalizing program.

Wooster believes that students with language based learning differences can achieve at high levels if they receive specialized instruction tailored to their unique needs, support that builds on their strengths and mitigate their challenges, and an environment that is engaging and sparks their desire to learn. Wooster believes that students’ learning experiences must be tailored to their individual needs, skills, and interests, and enable them to take ownership of their learning. Students at Wooster also develop deep connections to each other, their teachers, and other adults.

The work of the specialized tutor focuses on students with language based learning differences.

Specialized tutor responsibilities include (but not limited to):

  • Prepares and implements a strategic plan for ongoing intervention and remediation.
  • Supports efforts to ensure that the planning and implementation of services seamlessly meet the needs of students with disabilities, reduce the stigma of special education, and maximize accessibility to enable students with disabilities to meet high standards.
  • Remains current with accepted and appropriate instructional practice and research. This includes engaging in regular and strategic professional development.
  • Uses formative, interim, and summative assessments to document student progress and achievement; assesses and analyzes student strengths and needs; designs and implements appropriate instruction to facilitate learning and growth.
  • Gives input to teachers regarding student Progress Reports as deemed appropriate and necessary.
  • Be available and committed to ongoing verbal dialogue and conversations with the parents and the Wooster community.


  • Training in the Wilson Reading Program (certification preferred) or Orton-Gillingham certification
  • Training in Lindamood Bell’s Visualizing and Verbalizing
  • At least three (3) years of successful experience as an educator or reading tutor
  • Valid Teacher Certification (preferred)
  • Reading certification or working toward the successful completion of literacy certification (preferred)
  • Understanding of Wooster’s Vision: Purpose, Promise and Belief
  • Ability to model for, work with, plan with, and coach others.

Salary & Benefits

Salary is commensurate with work experience.

To Apply

Interested candidates should submit a cover letter, resume, and statement of philosophy to:

Elizabeth Higgins
Director of Teacher Learning

Substitute Teachers

Wooster School is looking for substitute teachers with teacher training and experience with students in grades K through 12th. For those interested in K through Grade 5, please send resumes and letter of interest to Mary Beth Brady at mary.beth.brady@woosterschool.org. For those interested in Grades 6 through Grade 12, please send resumes and letter of interest to Missy Munk at melissa.munk@woosterschool.org.

Wooster School is an Equal Opportunity Employer and we provide a work environment that welcomes diversity. In addition to a competitive salary, employees receive retirement, health insurance, tuition remission, short and long term disability and life insurance benefits.

All employees are subject to a criminal background check before any contractual offer is final.

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