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Position: Executive Director
Salary: $75,000-85,000 annual
Location: Middletown

Description: The Board of Directors of Oddfellows Playhouse seeks a dynamic and compassionate Executive Director to lead the organization with strategic vision. Reporting directly to the Board, the Executive Director serves as Chief Executive Officer, holding overall responsibility for the Playhouse’s staff, operations, and execution of its mission. We are dedicated to providing access to cutting-edge performing arts experience to young people of all socioeconomic backgrounds and seek a leader who will champion this cause The Executive Director is expected to develop a deep command of our community, programs, and culture to effectively guide the organization’s future. The ideal candidate combines a demonstrated passion for theater with the executive skills to successfully manage people, grants, resources, fund-raising, and budgets. The Board welcomes applicants who have experience in youth theater production and/or directing. While the position is primarily focused on organizational leadership and administration, there may be opportunities to direct or support productions based on experience and interest, in conversation with the Board and staff. Any such involvement would be optional, collaborative, and aligned with organizational needs. About Oddfellows Playhouse Oddfellows Playhouse, Inc. is a community arts organization founded in 1975 by Wesleyan University students and dedicated to empowering young people in Middletown, Connecticut, and the surrounding region. We currently serve over 1,500 young people annually through a variety of classes, productions, and immersive opportunities spanning theater, circus, dance, and visual arts. We are a small non-profit with 4 full-time staff (including the Executive Director) and annual revenue of approximately $700,000. Our activities include a year-round calendar of productions, after-school classes, and signature programs such as the celebrated Children’s Circus of Middletown (a five-week summer circus camp now in its 38th year). Key youth development and artistic ensembles include the Junior Repertory Company, Teen Repertory Company, Neighborhood-based Troupes, Oddbridge After-School program, and Circophony Teen Circus. Throughout its history, Oddfellows Playhouse has operated on the foundational belief that access to high-quality arts experiences is a fundamental right. Our commitment rests on a three-part mission that intertwines artistic excellence with social action: Artistic Excellence: To provide high-quality, cutting-edge theater created by and for young people. Educational Growth: To promote the development of young people—fostering skills, knowledge, and self-confidence—through the performing arts. Social Action & Equity: To promote the development of a truly multiracial, multicultural society by offering opportunities especially to underserved and at-risk youth, including five ongoing, neighborhood-based Troupes serving young people in public housing. Key Responsibilities Financial Management & Fundraising Government Relations: Cultivate and maintain critical relationships with state and local governments to secure public funding; manage compliance and reporting for all government contracts and grants. Development Strategy: Lead all revenue-generating activities, including grant writing, individual donor cultivation, corporate sponsorships, and annual fundraising campaigns. Budgeting: Develop and manage the annual operating budget, ensuring the organization operates within its financial means to maximize resources for programs. Strategic Leadership & Board Relations Vision & Planning: Collaborate with the Board of Directors to define the Playhouse’s strategic vision and long-term goals. Reporting: Serve as the primary liaison to the Board, providing transparent updates on financial health, fundraising progress, and organizational strategy. Governance: Support the Board in governance and recruitment of new Board members to ensure a strong, active leadership body. Staff Leadership & Operations Team Leadership: Lead, mentor, and support a small dedicated team, fostering a culture of collaboration, inclusivity, and accountability. Operational Oversight: Oversee the day-to-day operations of the Playhouse facility and administrative systems to ensure a safe and efficient environment for staff and students. Program Oversight & Community Engagement Artistic Partnership: Collaborate closely with the program directors to ensure all performance programming aligns with the mission, budget, and strategic goals of the Playhouse. At a minimum, the Executive Director is expected to have final determination authority over the artistic direction and season schedule of the Playhouse. Community Voice: Serve as the public face of Oddfellows Playhouse, building strong networks with community stakeholders, families, and peer arts organizations. Inclusion: Champion outreach initiatives that ensure the Playhouse reaches underserved populations and reflects the socioeconomic diversity of the community. Qualifications & Experience Required Qualifications Sector Leadership: Progressive leadership experience with non-profit arts organizations, demonstrating successful operational and strategic management. Mission Alignment: Demonstrated commitment to and direct experience with organizations dedicated to youth activities, performing arts, and social equity. Financial & Fundraising Acumen: Proven track record of securing major grants (government and foundation), leading successful fundraising campaigns, and robust fiscal management. Communication: Exceptional written and verbal communication skills, including public speaking and the ability to serve as the organization’s primary spokesperson to diverse audiences. Preferred Qualifications Education: Bachelor’s / Master’s degree in Arts Administration, Nonprofit Management, or related fields. Educational background or significant professional experience directly related to performing arts or theater. Experience successfully managing property/facilities used for performance or education. 

Benefits: Oddfellows offers a Health Reimbursement Account up to the maximum allowed by law for individuals and families and a 403(b) plan with a 3% match. 

Apply by Date: February 16, 2026

How to apply and process:  Candidates will be selected and interviewed by an Executive Search Committee established by the Board of Directors. The Board of Directors itself will make the final selection. We anticipate at least 2 rounds of interviews, during which you may be asked to provide professional references for the committee to contact. To Apply: Email a current resume and a cover letter to board@oddfellows.org. Please ensure your cover letter addresses how your background and experience corresponds to the required and preferred qualifications. Please also highlight any previous connections you have with Oddfellows Playhouse. Interviews will be conducted on a rolling basis with preference given to applications received on or before February 16, 2026.  Send resume to board@oddfellows.org

Position: Director of Before and After School (BAS) Program
Salary: $$80,000-90,000 annual
Location: Stamford

Description:  The Director of Before/After School Programs provides strategic and operational leadership for the development, coordination, execution, and assessment of a continuum of high-quality programs serving school-age children, aligned with ROSCCO’s mission, We Build Strong Young People. This role serves as a senior resource and technical advisor to the Executive and Managing Directors and ensures the delivery of compliant, effective, and innovative programming. The Director sets programmatic goals, manages staff, oversees operations, secures resources, and maintains full compliance with all accrediting, licensing, and funding requirements, with particular emphasis on Connecticut Office of Early Childhood (OEC) licensing regulations and procedures.

Essential Tasks & Responsibilities: Program Development and Management

• Lead the development, implementation, and evaluation of programmatic goals, strategies, and action plans to ensure consistent, high-quality ROSCCO programs across all sites.
• Use outcome data, assessments, and program evaluations to measure impact, guide continuous quality improvement, and foster innovation in program delivery.
• Collaborate with the Executive Director and Managing Director to ensure program planning aligns with ROSCCO’s strategic priorities and organizational initiatives.
• Oversee the design, implementation, and management of programs that enhance quality, visibility, and student outcomes.
• Supervise and track bi-weekly staff work schedules, making necessary revisions and approvals prior to payroll processing.
• Communicate effectively and professionally with parents and guardians regarding student concerns, behavioral issues, and program matters requiring attention or intervention.
• Serve as the primary point of initial welcome, intake coordination, and acknowledgement for families of children with IEPs, ensuring inclusive and responsive programming.
• Lead the recruitment, onboarding, and credentialing of approximately thirty-five staff annually, including criminal and medical clearances, payroll documentation, policy orientation, pre-service training, and completion of all mandated certifications required by Care 4 Kids and CT OEC. Licensing, Compliance & Regulatory Oversight
• Demonstrate strong working knowledge of Connecticut Office of Early Childhood (OEC) licensing regulations and procedures for school-age child care programs.
• Serve as the organization’s primary licensing lead for before- and after-school programs, ensuring full compliance with all state, federal, accrediting, and funding requirements.
• Prepare for, coordinate, and lead all OEC licensing visits, inspections, monitoring reviews, and corrective action processes. • Maintain accurate and up-to-date licensing documentation, staff credential files, training records, health and safety compliance files, and monitoring reports across all program sites.
• Provide technical guidance and training to site coordinators and staff regarding licensing standards, regulatory changes, and compliance expectations. Staff Leadership, Supervision & Team Building
• Provide strong managerial leadership and direct supervision to site coordinators and part-time school-age childcare staff, fostering a collaborative, accountable, and high-performing team culture.
• Recruit, train, mentor, evaluate, and support staff to promote professional growth, leadership development, and program excellence.
• Schedule and facilitate monthly staff meetings, trainings, and special meetings as needed.
• Ensure staffing patterns, qualifications, and supervision ratios meet all licensing, certification, and organizational requirements.
• Address performance concerns, disciplinary actions, and corrective plans in alignment with organizational policy and employment law. Financial Management & Resource Development
• Oversee the development, management, and monitoring of program budgets to ensure fiscal responsibility and alignment with organizational goals.
• Track staffing costs, program expenditures, and resource needs in collaboration with senior leadership and the finance department.
• Identify funding opportunities and collaborate with the Executive Director and development staff to secure grants, contracts, and other revenue sources.
• Ensure all programs and staff comply with financial, contractual, licensing, and funding requirements. Operations & Program Coordination
• Lead the planning and implementation of daily operations and scheduled program activities across multiple sites.
• Ensure timely procurement, distribution, and inventory of program supplies, materials, and equipment.
• Maintain strong organizational systems to manage enrollment, attendance, staffing coverage, licensing compliance, and reporting requirements.
• Ensure effective communication with staff and families by creating and distributing monthly calendars, newsletters, letters, flyers, memos, and program updates.
• Serve as a liaison to community partners, school administrators, and collaborating agencies as requested by the Executive and Managing Directors. Relationship & Partnership Management
• Develop and maintain strong working relationships with the ROSCCO Executive Director, Managing Director, Stamford Public Schools administration, school principals, teachers, staff, families, and children.
• Represent ROSCCO in school meetings, community forums, and partnership initiatives to strengthen program visibility, reputation, and impact.
• Actively engage community stakeholders to expand partnerships and enhance program reach and quality.

Directly supervises site coordinators and school-age childcare staff. Responsible for recruitment, training, performance evaluation, coaching, and corrective action. Provides leadership and guidance to ensure adherence to licensing regulations, organizational policies, and program standards while supporting staff professional growth and team development.

Qualifications: 

• Master’s degree in Education, Early Childhood Education, Child Development, Public Administration, or a related field preferred.
• Minimum of five (5) years of progressively responsible experience in out-of-school time, early childhood, or youth program administration and management.
• Demonstrated experience with nonprofit management and public and private funding processes.
• Strong, demonstrated knowledge of Connecticut Office of Early Childhood (OEC) licensing regulations and procedures for school-age child care programs, including inspection and compliance processes.

Apply by Date: February 26, 2026