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

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. Compensation & Application Salary Range: $75,000 – $85,000 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 Process & How to Apply 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.

Apply by Date: February 2026