Founded in 1926, Wooster School is a co-educational, 4-12, college preparatory day school with an enrollment of approximately 350 students, and a regional leader in student-centered education. The School is located in Danbury, Connecticut. By design and mission, it educates a student population diverse in academic ability, socioeconomic background, religious affinity, and race and ethnicity. Wooster is a member of the Connecticut Association of Independent Schools and the National Association of Independent Schools.

While Wooster’s traditions of self-help and relationship-building have long been recognized as strengths, our more recent commitment to innovative approaches to teaching and learning are making us a leader in the independent school world. We are committed to a learner-centered environment for our students, and to exploring the full potential of competency-based and personalized teaching and learning.

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.

Head Varsity Hockey Coach

Position Description

Wooster School seeks a Head Varsity Hockey Coach for the Winter Season from 11/15/21 - 3/11/22. The ideal candidate will have hockey coaching experience at the high school and/or youth level. The ideal candidate will have experience working with a school team in grades 7-12 as a coach and/or teacher. They should demonstrate a flexible, positive, can-do disposition that translates to the ice. The coach will work with the Athletic Department to ensure that the hockey program is reflective of overall Wooster School experience for our student-athletes. The position is an extension of the classroom and the candidate should be able to demonstrate the ability to teach players in a positive manner and be a role model as well.

The Role

Head Varsity Hockey Coach:

  • Attend practices 3-4 days per week (usually 7:00 - 8:00 am)
  • Attend all games as per the Wooster Hockey schedule
  • Responsible for practice design and execution
  • Responsible for game management
  • CPR and First Aid Certification required

Salary & Benefits

This is a part-time position. Salaries are competitive with local independent schools.

Interested candidates should submit a cover letter and resume to:
Jeff Carone, Director of Athletics


Position Description

Wooster School seeks a full-time Controller for its Business Office. The Business Office consists of three full time professionals: a Bursar, Controller and CFO. The office utilizes Blackbaud Accounting software. The office administers an operating budget of approximately $10.5 million and works on a broad range of operational issues that expands the scope of the department’s responsibilities broadly beyond the general ledger, A/P, A/R, payroll and benefits. A sampling of these includes:

  • Responsibility for managing the daily activities of the Maintenance Department.
  • Planning and managing all capital and construction projects.
  • Administering Faculty and Staff safety and best practices training.
  • Assist the Admissions Department in establishing Financial Aid.
  • Strategic Modeling and Planning for the Head of School and Board of Trustees.

In addition to possessing a strong accounting background, the successful candidate will be an individual that wishes to grow their career in independent school operations and business affairs. They will have the curiosity and motivation to expand their duties into leadership areas. They will also have a desire to leverage technology to help Wooster’s Business Office to be more efficient and seamlessly integrated into the school.

The Controller is a salaried position and reports directly to the CFO. The primary duty of this position is to be responsible for the school’s financial reporting system to ensure that Wooster’s general ledger is accurate, current and maintained in accordance with GAAP and best practice. Secondary duties include administration of accounts payable and payroll.

It should be noted that in a Business Office of this size where the professionals work closely, and cross support and train, the office is dynamic in responding to changes in structure to accommodate the needs of the school and the interests and talents of team members.

Primary Duties and Responsibilities

Reconciliations, Journal Entries, Audits and Financial Reports
  • Record all the school’s financial transactions in a timely manner for accounts receivable, accounts payable, cash receipts, payroll, cash, gift entry, release from restriction entries and transfers.
  • Reconcile all bank and investment accounts monthly
  • Reconcile all giving monthly
  • Responsible for all journal entries
  • Support CFO in preparation of monthly and quarterly reports
  • Support Auditor and Audit Committee in annual audit, Form 990 and 5500 filing
  • Maintain Investment Summary, Unitization of Endowment and Quasi Endowment Funds, G&A Allocation and temporary restricted giving/net asset schedules
Accounts Payable and Budgets
  • Manage Accounts payable process.
  • Manage departmental budgets and reporting to departments and the Head of School.
Payroll, Benefits, and Training
  • On a biweekly basis input payroll. Enter hourly employees, coach’s stipends, substitutes, tutoring and other misc. payroll checks into the system and administer benefit deductions as necessary.
  • Maintain employee paid benefit time records
  • Work with the Business Office team to document compliance with mandatory training requirements.

Human Resources Coordinator Responsibilities - Stipend to Controller

This is an associate administrator position under general supervision of the Chief Financial Officer and/or the Head of Schools. The incumbent of this position is responsible for administering personnel records, related paperwork, and benefit enrollments for all employees including all educators, staff, coaches, tutors, substitute teachers and administrators. Responsibilities include administering enrollments (including open enrollments) into employee benefits, all aspects of distributing and collecting hiring packets, offer letters, background checks and other related documentation as well as records necessary to comply with Department of Labor, State of Connecticut and or Federal regulations.

Examples of work (Illustrative Only)
  • Update as needed, distribute, collect and process all forms included in the “New Employee Packet” (Wooster Application, Privacy Statements, Research Services Form, VECH Criminal History Waiver and Consent form, Fingerprint Card, DCF Release Form, Education Employer Verification form,, Payroll forms)
  • Maintain and implement employee benefits programs, including but not limited to overseeing enrollment and/or disenrollment, answering questions related to benefits offered and maintains census data related to all benefits programs;
  • Establish, conduct and ensure all employees complete employee training programs as related to mandated training;
  • Prepare organizational charts of the various departments in the School;
  • Collect salary information paid by other organizations as well as benefit packages offered by other organizations to help ensure that our salaries and benefits are competitive;
  • Ensure legal compliance by monitoring and implementing applicable human resources federal and state requirements;
  • Represent the school at unemployment hearings;
  • Maintain management guidelines by preparing, updating and recommending human resources policies and procedures;
  • Conduct special studies on employee benefits, working conditions, and methods of work as requested and directed;
  • Prepare, distribute and collect all annual offer letters and new offer letters for all employees;
  • Maintains personnel files in accordance with best practice;
  • Administer leaves of absence [FMLA, Worker Compensation leaves (not claim work) other], and oversee and establish compliance, processes and procedures for maintaining accurate records of sick leave, vacation leave, etc.;
  • Maintain an accurate up to date list of every employee, their position, benefits and their rate of pay at all times;
  • Use computer applications or other automated systems such as spreadsheets, word processing, calendar, e-mail and database software to streamline and/or perform related work assignments;
  • Collaborate with other staff as necessary to approve access to and/or remove access to the Wooster School computer network, email and telephone;
  • Print or cause to be printed (i.e., directs technology staff to print) and distributed id badges as necessary
  • Do related work as required.

Minimum Requirements

  • Bachelor’s Degree in Accounting or Business Administration
  • CPA or Masters in Accounting
  • Not-for-profit fund accounting experience
  • Experience with accounting software and a demonstrated ability to customize and generate reports and statements
  • The ability and willingness to cover a broad range of Business Office duties and the flexibility to respond to the challenges of being an integral part of a small and busy office
  • A commitment to learning the entire scope of Business Office duties
  • Ability to handle confidential information with total discretion
  • Effective written and oral communication skills
  • Outstanding interpersonal skills
  • A love of children and school environments
  • The wisdom, experience, and sensitivity to effectively communicate with and support all of the school’s constituencies: parents, students, faculty and staff, alumni, and the Board of Trustees
  • Patience, flexibility, creativity, integrity, and a profound sense of humor

Other Related Requirements

  • A resume and personal statement.
  • Three professional references must be provided upon request.

Compensation & Benefits

Wooster School salaries are based on years of experience and special expertise. Wooster additionally compensates faculty for various afternoon activities based on the time commitment required. A competitive benefits package includes retirement, health insurance, tuition remission, short and long-term disability, and life insurance.

Interested candidates should submit a cover letter and resume to:
Michael Jumper, CFO

Technology, Making, and Design Teacher

Position Description

Wooster School seeks a Technology, Making, and Design Teacher (TMDT) with an advanced degree and teaching experience, who can partner with the Director of Curriculum and Department Coordinators to co-construct a vision and direction for the Technology, Making, and Design program within our Middle and Upper School. This position involves developing and teaching year-long Technology, Making, and Design courses at the Middle School level, wherein the curriculum offers students a cohesive experience that prepares them for 21st century challenges. Additionally, the TMDT has also offered various Upper School electives, including: Open Makerspace, Engineering & Design, Woodworking, Arduino, Introduction to Coding, and Digital Media. More holistically, this instructor will collaborate with grade level teacher teams to enhance project-based learning experiences for grades 5-9. The ideal candidate has a strong grounding in design, systems, coding, and making, and is a curious student of the art and science of teaching and learning. Demonstrating a positive, can-do disposition and strong sense of humor is also essential. As part of a school-wide instructional focus, the ideal candidate also has experience with, or an interest in learning about, personalized instruction, rooted in offering multiple pathways to competency in recognition of the jagged profiles of learners.

The Role

Full-time Wooster teachers:

  • Teach Technology, Making, and Design courses to all students in grades 5-8 and offer various electives courses (as designed by the instructor) in the Upper School
  • Participate in student-focused programs such as: advisory, chapel, community meals, and clubs
  • Demonstrate a commitment to lifelong learning through continued professional development
  • Commit to designing culturally responsive curricula and experiences in collaboration with our Center for Equity and Justice

Salary & Benefits

This is a full-time, exempt position. Salaries are competitive with local independent schools. A competitive benefits package includes retirement, health insurance, tuition remission, short and long-term disability, and life insurance.

Interested candidates should submit a cover letter, resume, and statement of philosophy to:
Parvin Taraz, Director of Curriculum

Director of Annual Giving and Community Relations

Position Description

Working closely with our Development, Marketing, and Communications team, the Director of Annual Giving and Community Relations is responsible for our Annual Appeal and community events, in addition to acting as the primary liaison with our Parents’ Association.


  • Oversee Wooster’s Annual Appeal, collaborating on strategy, messaging, and content development for all constituencies and channels.
  • Manage the event planning of our community events. (e.g., New Family Orientation, New Family Picnic, Giving Day, and the annual Gala)
  • Steward existing donors and develop new ways to acknowledge giving, celebrate the community, foster relationships, and cultivate new donors.
  • Contribute to the creation of a bi-weekly Advancement Report to be shared with Senior Leadership.
  • Oversee and manage the creation of the Annual Report, working with the Advancement Associate to publicly acknowledge previous year’s giving.


  • Bachelor’s degree is required.
  • Previous experience with Blackbaud’s Raiser's Edge is required.
  • Proficiency in basic data management systems and computer applications. Facility with the Google suite, especially Spreadsheets and Slides, is a significant plus.
  • Willingness and ability to keep pace with technological and software advances.
  • Knowledge of prospect management and development operations.
  • Ability to work independently and as part of a team: to lead and to follow.
  • Excellent organizational skills and the ability to manage multiple projects simultaneously.
  • Ability to handle sensitive and confidential matters with appropriate discretion.
  • Willingness and ability to work a flexible schedule, including occasional evenings and weekends.
  • High personal standards, an attention to detail, and a collaborative, can-do, and positive disposition.
  • The desire to learn about and contribute to our school outside of immediate job responsibilities.

Salary & Benefits

This is a full-time, exempt position. Salaries are competitive with local independent schools. A competitive benefits package includes retirement, health insurance, tuition remission, short and long-term disability, and life insurance.

Interested candidates should submit a cover letter and resume to:
Christopher Pannone, Associate Head of School

School Chaplain

Position Description

Reporting directly to the Head of School, the School Chaplain is a key member of Wooster’s faculty and administration, a member of the Head of School’s Cabinet, and plays a prominent role in all aspects of school life. Working across all grade levels and all school constituencies, the School Chaplain is a chief articulator of Wooster’s foundational values, a central connector and builder of community, a source of pastoral care, and a leader of the spiritual life of the school. Our ideal candidate is a learner-centered teacher with a deep appreciation of schools and children of all ages. The Chaplain should also be a life-long learner and relationship and consensus-builder. As the spiritual guide for the community, the Chaplain is also a person of faith who can help young people understand and navigate the complexities of religion and spirituality, both historically and in the modern context. Finally, the Chaplain is committed to individual and collective service to our local community and world.


  • Oversees our weekly Chapel meetings and works with faculty, administration, and students to create accessible, interesting, and learner-centered programming.
  • Mentors our James Marshall Chapel Society Prefect and society members, and helps them find their voice and role in community service and engagement.
  • Manages and supervises Wooster School’s “Hours for Others” community service program.
Community Stewardship & Pastoral Care
  • Acts as a visible, positive, and affirming presence in the school community, throughout the day and at school events, and with all community constituents.
  • Creatively brainstorms ideas for collaborative service and enrichment opportunities with faculty, students, parents, and administration, and our broader Danbury community.
  • Takes the lead in providing care for community members who are experiencing hardship or tragedy in their lives, while also working closely with the Parents’ Association to organize additional support as needed.
Teaching & Advising
  • Open to developing and teaching courses in world religions, history of religions, ethics and morality, philosophy, faith and spirituality, and other personal areas of academic interest, including in our Deep Learning Initiative.
  • Leads a section in our Senior Seminar program, collaborating with our Dean of Students and Director of College Guidance to develop and deliver an engaging college and life preparatory curriculum.
  • Advises a cohort of students in either or both our Middle and Upper Schools.

Salary & Benefits

This is a full-time, exempt position. Salaries are competitive with local independent schools. A competitive benefits package includes retirement, health insurance, tuition remission, short and long-term disability, and life insurance.

Interested candidates should submit a cover letter, resume, and statement of philosophy to:
Christopher Pannone, Associate Head of School

Substitute Teachers

Wooster School is looking for substitute teachers with teacher training and experience with students in grades 4th through 12th. Please send resumes and letter of interest to Mary Beth Brady at mary.beth.brady@woosterschool.org.

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