Deputy Director (Grievance)

The Chicago Teachers Union (CTU) is seeking a dynamic, collaborative, and justice-driven organizer or educator to join our team as the Deputy Grievance Director.

The Chicago Teachers Union is a transformative labor union of nearly 30,000 teachers, paraprofessionals, clinicians, and staff in the Chicago Public Schools and charter schools. We are a global leader in the fight for educational justice, racial equity, economic justice, workers’ power and the right of all students, all people, and all communities to thrive.

This is a unique opportunity to support and advocate for rank-and-file members through direct workplace representation, contract enforcement, and strategic organizing. The ideal candidate is deeply committed to educational and racial justice, has strong experience in labor or community advocacy, and is ready to help defend and expand the rights of public educators in Chicago’s schools.

The Deputy Grievance Director supports the Grievance Director in advancing member rights through effective contract enforcement, grievance handling, and advocacy. This role plays a critical part in ensuring members are treated fairly; workplace issues are addressed with urgency and integrity, and that collective bargaining agreements are respected. The ideal candidate will be a strong communicator, strategic thinker, and committed advocate for justice in the workplace.

Primary Responsibilities

• Assist the Grievance Director in managing the grievance process, including intake, investigation, documentation, and resolution.
• Support school-site union representatives in resolving workplace issues informally and formally.
• Track and analyze trends in workplace issues to inform organizational strategy and bargaining priorities.
• Conduct training sessions for building representatives and members on grievance procedures, member rights, and workplace protections.
• Collaborate with legal counsel and union leadership on arbitration preparation and complex cases.
• Assist in maintaining a grievance database, ensuring accurate and confidential record-keeping.
• Advocate for a grievance process that is inclusive, trauma-informed, and accessible to all members, especially those from historically marginalized communities.
• Engage with members at worksites to build relationships and identify emerging issues.

Essential Qualifications

• 5 years experience in case management, human resources, social work, teaching/education, youth development, labor movement, and/or social justice.
• 3 years of people and/or project management experience; demonstrated success in leading departments, diverse teams, and managing complex projects.
• Some familiarity with Chicago’s education and political landscape.
• Demonstrated commitment to labor rights, social justice, and educational equity.
• Experience in grievance handling, labor organizing, or related advocacy work.
• Strong interpersonal, negotiation, and conflict resolution skills.
• Knowledge of collective bargaining agreements and workplace rights.
• Ability to communicate effectively across lines of race, class, language, and gender identity.
• Excellent organizational and documentation skills.
• Ability to work independently and as part of a team in a fast-paced environment.
• Willingness to work irregular hours, including evenings and weekends.

Desired Qualifications

• Bilingual
• Knowledge of public education issues and the challenges faced by teachers.
• Familiarity with collective bargaining, labor law, and union structures.
• Prior experience in union representation or labor advocacy.
• Familiarity with school district policies, employee discipline procedures, and education law.
• Experience working within or with urban public education systems.
• Familiarity with trauma-informed approaches and restorative practices.
• Legal training or paralegal experience a plus, but not required.

If you do not meet all of the required qualifications, but believe this role is right for you, please apply, but be sure to uplift all experience that align with both essential and desired qualifications.

Location & Hours of Operations

CTU’s hours of operation are Monday - Friday 9 am - 5 pm cst, plus weekends and evenings as the work dictates.

The Deputy Grievance Director is expected to work onsite at CTU Headquarters daily.

• Employer subsidized medical, dental, and vision insurances
• Employer Contributed 401(k)
• 3 Weeks' Vacation Time First Year
• Short Term Disability
• Health Savings Account /Dependent Care Flexible Spending
• Cell Phone Stipend

Bilingual preferred, but not required.