Connecticut Education Association
an affiliate of the National Education Association

Deputy Executive Director

Based in Hartford, CT

 

About Us:
As Connecticut’s largest and strongest union of certified educators, the Connecticut Education Association (CEA) makes the biggest difference in the lives of teachers, the success of students, and the quality of the public education in Connecticut. We empower teachers so that they can excel at educating all students.

CEA champions competitive salaries and benefits, well-resourced classrooms, and safe, healthy schools to attract and retain the best teachers. We further protect the rights of educators with expert representation.

The Deputy Executive Director serves as a key strategic and operational partner to the senior director’s leadership team. This role supports the execution of CEA’s mission, strategic priorities, and organizational effectiveness. The Deputy Executive Director provides executive-level leadership, operational oversight, and strategic direction across assigned divisions and organizational initiatives in a collaborative, mission-driven, and unionized environment.

Duties and Responsibilities:
Strategic Leadership & Execution 

• Partner with the leadership team to develop and implement organizational strategy, priorities, and long-term planning initiatives.
• Translate strategic goals into operational plans, ensuring alignment across departments and governance structures.
• Monitor progress toward organizational goals and adjust strategies to respond to emerging challenges and opportunities.
• Lead high-priority organizational initiatives as assigned.

Operational Oversight 

• Oversee assigned divisions, departments, or functional areas, ensuring effective administration and performance outcomes.
• Drive operational excellence by improving systems, workflows, and organizational effectiveness.
• Collaborate with leadership, staff, and governance to ensure coordination across departments, including field operations, government relations, communications, member services, advocacy, and other internal functions.

Labor Relations & Union Environment Leadership 

• Provide leadership in a unionized environment, including collective bargaining and labor-management relations.
• Partner with leadership and staff unions to ensure compliance with union contracts and employment law.
• Support a culture of collaboration, respect, and effective labor-management communication, while managing with labor values.

Governance & Board Relations

• Support the Executive Director in working with the Board of Directors, Executive Committee, and Representative Assembly.
• Attend governance meetings and serve as a resource to leadership.
• Assist in preparing materials, reports, and recommendations for governance bodies.

External Relations & Representation

• Represent CEA in external settings, including coalition work and stakeholder engagement.
• Build relationships with affiliated organizations and community partners.

Leadership & Talent Management 

• Develop assigned staff and leadership team members.
• Support performance management, coaching, and succession planning.
• Foster a high-performing, inclusive, and mission-driven organizational culture.
• Participate in workforce planning and employment interviews.

Organizational Planning & Change Management 

• Lead organizational development initiatives.
• Support restructuring, change management, and workforce alignment.

Acting Executive Director Responsibilities 

• Serve as surrogate to the Executive Director when designated.

Other Duties

• Other professional duties as assigned.

Education: 

• Bachelor’s degree required.
• Master’s degree in labor relations, public administration, education, law, or related field strongly preferred.

Preferred Qualifications:

• 5–10 years of progressive leadership experience.
• Senior-level leadership experience in a labor union, education association, nonprofit, or similar organization.
• Experience managing departments or divisions.
• Experience in labor relations and union environments.
• Experience working with governance structures.
• Demonstrated commitment to public education and union values.
• Equivalent combination of education and experience may be considered.

Core Skills & Competencies: 

• Executive Leadership & Strategic Vision – Provides enterprise-level leadership aligned with CEA’s mission, vision, and strategic priorities. Demonstrates sound judgment, strategic thinking, and the ability to lead complex organizational initiatives.
• Labor Relations & Union Leadership – Demonstrates strong knowledge of labor union operations and collective bargaining environments. Navigates labor-management relationships and supports collaborative problem-solving.
• Organizational Leadership & Change Management – Leads organizational initiatives and supports change management across departments. Builds alignment among leadership, staff, and governance bodies.
• Operational & Financial Acumen – Oversees multiple functions and supports budget planning, resource allocation, and operational effectiveness aligned with strategic priorities.
• Governance & Political Acumen – Works effectively with governance bodies, executive leadership, and membership. Demonstrates diplomacy and sound decision-making in complex environments.
• Relationship Building & Stakeholder Engagement – Builds trusted relationships across leadership, staff, members, governance, and external partners. Demonstrates strong collaboration and influence traits.
• Strategic Communication & Executive Presence – Communicates effectively with leadership, governance, staff, and external stakeholders. Demonstrates professionalism and executive presence.
• Decision Making & Problem Solving – Applies sound judgment and analytical thinking to complex challenges. Make informed and timely decisions.
• Adaptability & Resilience – Responds effectively to changing priorities while maintaining leadership effectiveness.
• Technology & Organizational Effectiveness – Leverages data and technology to support decision-making and operational improvement.

Reports To:
Executive Director 

Work Environment:
The work is primarily performed in an office environment located at CEA Headquarters in Hartford, Connecticut. Reasonable accommodations will be provided to enable individuals with disabilities to perform essential functions. Travel, weekend, and evening work expected.

Pay and Benefits:
The starting salary is $214,819 in accordance with Director-Level Policies. We offer a comprehensive benefits package, including medical, dental, and vision coverage; a 401(k) and pension plan; 16 paid holidays; as well as vacation and sick time. 

Equal Opportunity:
CEA is proud to be an Equal Opportunity Employer, committed to building a workplace culture rooted in diversity, equity, inclusion, and belonging. We strongly encourage applications from individuals who identify as people of color, LGBTQ+, people with disabilities, veterans, and others from historically underrepresented backgrounds. 

Individuals with disabilities requiring accommodations in the application and interview process should contact Latisha Billups at latishab@cea.org. 

To Apply:
All external applications should be submitted HERE.