POSITION ANNOUNCEMENT

Application Deadline: January 15, 2026

Job Title: Executive Director

Hours: Full time salaried position, 40 hours/week

Location: Holyoke, MA

Anticipated Start Date: March 2, 2026

Enchanted Circle, a 50 year strong non-profit in Holyoke, MA, seeks an Executive Director with a strong commitment to arts and education in Western Massachusetts. The next Executive Director will build and sustain strong partnerships, listen deeply to community voices, and champion collaborations across the region and beyond. They will work to bridge the arts, education, and social emotional wellbeing with families, schools and communities in Holyoke and Hampden County.

Historically, the Executive Director has overseen both artistic and strategic functions. We are now seeking a leader with exceptional strategic, operational, and organizational development skills to build a strong foundation for the future. This executive will be knowledgeable about the administration of an arts education organization, and adept at creating strategic partnerships and collaborations that enrich our collective arts community.

In the first year, the new Executive Director will focus on fundraising and budgeting, hiring 1-2 additional staff, and partnering with consultants, board and community stakeholders to develop a new strategic plan. They will also collaborate with a future curriculum or program director to shape new programs, assemble artistic and educational teams, and plan for the re-launch of organizational programming.

HISTORY & MISSION

Enchanted Circle is a 501(c)3 Arts Integration organization bridging the arts, education, and social-emotional wellbeing. Based in Holyoke, Massachusetts, Enchanted Circle was founded as Enchanted Circle Theater in 1976, and has been a regional leader in the field of arts integration, using the arts as a dynamic teaching tool in the classroom, on the stage, and in community. Culturally responsive arts integration offers all learners a holistic and creative approach to education, one that is accessible and equitable, which connects us to ourselves, to one another and to our world. These values guide our partnerships with schools, community organizations, human service agencies, and local leaders throughout Massachusetts.

PROGRAMS

Professional Development: For more than three decades, Enchanted Circle has trained PreK-12 educators and youth service professionals to integrate the arts across curricula. Our workshops offer both theoretical and practical applications to enhance academic learning, social emotional wellbeing, and collaborative teams.

Community Collaborations: Enchanted Circle partners with community organizations to co-create arts-integrated projects that respond to local needs and emphasize literacy, history, the environment, and/or social justice. These projects range from original performances, intergenerational art-making days, teen arts labs, and community murals.

School Partnerships: Teaching Artists work directly in the classroom with students and teachers, integrating the arts into content areas like math, science, social studies, literature and language arts. Classroom-based residencies range from short-term to year-long partnerships, and focus on promoting creative and critical thinking.

Creative Youth Development: Our creative youth development programs build artistic skills, leadership, trust, empathy, and community connection through culturally relevant programming.

Digital Resources: Our digital storytelling library hosts hands-on arts integration resources and the Social Justice Movers & Shakers Online free platform for teachers and students.

KEY RESPONSIBILITIES OF THE EXECUTIVE DIRECTOR

In the first 1-2 years, the executive director will be primarily focused on strategic and systems development responsibilities, with a heavy percentage of effort on the following:

• Reestablish the organization’s presence across Holyoke, Springfield, and the region through active community engagement with families, educators, artists, donors, former and new partners, and civic leaders.
• Lead external communications, storytelling, public relations, and organizational messaging.
• Collaboratively design and implement a comprehensive fundraising strategy, including major donor cultivation, solicitation, and stewardship.
• Develop long-term strategy and vision in partnership with the Board, staff and relevant stakeholders.
• Ensure the organization’s financial health by leading annual budgeting, financial monitoring, and long-term fiscal planning.
• Establish organizational systems, processes, and infrastructure to support stability and growth.
• Work closely with the Board Chair and board members to support strong governance and board development.

The executive director will also oversee additional duties as a secondary focus, including:

• Foster a supportive, collaborative internal culture centered on staff development, learning, and wellbeing.
• Hire, supervise, and support staff and contractors; develop organizational structure, roles, and workflows.
• Provide artistic and programmatic leadership in assessing community needs and shaping programming priorities.
• Stay abreast of developments in arts education to guide the organization’s artistic and educational direction.

QUALIFICATIONS

• Demonstrated success in fundraising, including donor cultivation and solicitation.
• Strong financial management skills, including budgeting and forecasting
• Arts administration experience
• Fluent Spanish and English required
• Experience with managing, supporting and leading staff, including familiarity with HR Compliance; ability to listen to the staff and community
• Experience with collaborative strategic visioning, planning and implementation
• Public relations experience, including public speaking and crafting compelling messaging in support of organizational mission

DESIRED SKILLS & COMPETENCIES

• Ability to communicate effectively and build trusting relationships across diverse communities, while learning alongside the rich local and regional cultures across Holyoke, Springfield and Western Massachusetts.
• Strong ability to set priorities and manage multiple projects and staff.
• Artistic background and/or passion for the arts and arts education.
• Skilled storyteller who can articulate the organization’s impact to build partnerships and donor support
• Be able to create a forward-thinking, long-term vision for the organization, tap into innovative thinking, and help Enchanted Circle craft a future vision
• Commitment to shared leadership, collaborative decision-making, and community-centered practices.

COMPENSATION & LOCATION

Salary range: $75-83,000.

Benefits: Two weeks PTO, up to 3% match on Empower CORE 401K, and a professional development budget.

Location & Travel: This is an in-person role based in Holyoke, with regional travel within Hampden County and occasional statewide travel.

APPLICATION INSTRUCTIONS & REFERRALS

Think Again Training & Consulting is supporting Enchanted Circle’s executive search and leadership transition. We work with purpose-driven organizations to help them build just, equitable and sustainable processes and systems. You can find more about our work or reach out via our website: thinkagaintraining.com

Applications should include the items listed below as a single, combined PDF:

Cover letter detailing your prior relevant experience and interest.
Resume or CV
List of three references (will not be contacted without prior notice)

Please submit applications, referrals, or requests for a confidential conversation to: meiver@thinkagaintraining.com. Applications are due by January 15th, 2026, by 5pm EST.

Selected applicants will begin to be contacted for interviews in late January / early February of 2026. Applications may be reviewed over time, so please be patient if you do not hear from us immediately.

Enchanted Circle strongly encourages applications from candidates who may not meet every listed qualification but feel inspired by our mission, and who bring relevant lived or professional experience, and believe they can fulfill the role and meet our needs. We recognize that skills and strengths develop in many ways—through related jobs, community work, caregiving, artistic practice, education, organizing, and professional roles inside or outside the arts or nonprofit sectors. If you are excited about the role and believe you have the ability to contribute to the future of Enchanted Circle, we encourage you to apply. We welcome candidates who bring curiosity, creativity, and a commitment to growth, in partnership with the communities we serve.

EQUAL OPPORTUNITY EMPLOYER STATEMENT

Enchanted Circle is an Equal Opportunity Employer, in accordance with all relevant laws. We do not discriminate on the basis of race, color, religion, creed, national origin, ancestry, gender identity or expression, sexual orientation, age, disability, genetic information, marital status, veteran status, citizenship, or any other characteristic (whether or not it is protected by law). We are committed to building a diverse and inclusive team and strongly encourage individuals from historically marginalized or underrepresented communities to apply.

COMMITMENT TO RACIAL JUSTICE AND SOCIAL JUSTICE STATEMENT

At Enchanted Circle, our work is rooted in the belief that creativity, storytelling, and the arts are powerful tools for educational development, growth, equity, connection, and healing. We are committed to advancing justice through our programs, partnerships, and organizational culture. We strive to ensure that our leadership, staff, and artistic teams reflect the diverse communities of Holyoke, Springfield, and Western Massachusetts, and we actively work to dismantle barriers that limit access, participation, or belonging. We embrace shared learning, accountability, and community collaboration as essential components of our mission. This includes a commitment to anti-racism, and supporting racial equity in our work and programs.