Chicago Teachers Union - Chief of Staff

The Chicago Teachers Union (CTU) is seeking a dynamic, collaborative, and experienced leader and exceptional manager of people to become its Chief of Staff. 

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. 

As a core member of CTU’s leadership team, the Chief of Staff reports to the union President and works with CTU’s Officers to turn vision into practical action—championing inclusive, transparent, liberatory, and sustainable systems that cultivate and maintain a culture of accountability and deliver measurable impact with efficiency and purpose.
 

Primary Responsibilities

• Change Management & Organizational Leadership: 
  • Develop and implement strategic plans with clear priorities, timelines,  measurable outcomes, and are responsive to evolving political, educational, and community contexts.
  • Lead internal change management with a focus on collaboration, equity, transparency, and sustainability across CTU teams.
  • Assess and reform internal practices that perpetuate inequity, inefficiency, or exclusionary cultural norms.
• Team Management & Development: 
  • Lead and manage CTU’s internal operations, including direct supervision of designated teams (which may shift or expand as dictated by organizational need).
  • Assess organizational capacity and lead staff planning, hiring and evaluation processes, and team structure development;
  • Manage process to ensure all staff have development and support plans to cultivate a sustainable and leaderful movement.
• Risk Management & Compliance: 
  • Identifying potential risks to the organization (financial, reputational, operational) and developing strategies to mitigate them. 
  • Work with operations, finance, and human resources team leads to ensure compliance needs are met (internally and externally).
• Evaluation and Impact: 
  • Implement and manage systems for tracking progress toward strategic goals and outcomes.
  • Facilitate consistent evaluation, reflection, and reporting to strengthen organizational impact, reach, and accountability.

Though their primary focus is internal, on building and managing the culture and staff within CTU, the Chief of Staff will, as needed, lead execution on external and special initiatives. 

Essential Qualifications

• 8 years senior or executive leadership experience in mission-driven, labor, nonprofit, or advocacy organizations.
• 5 years of experience managing diverse people and teams, with a track record of building cultures of collaboration, inclusion, support, and accountability.
• Commitment to CTU’s mission, including public education, racial justice, economic justice, and labor solidarity.
• Experience leading  organizational change with a deep understanding of equity, belonging, anti-oppression, and inclusive leadership practices; ability to operationalize values of justice and inclusion.
• Ability to analyze complex issues and translate them into clear, actionable strategies or tactics - connecting strategy to execution across departments and teams.
• Excellent interpersonal, facilitation, and communication skills—with the ability to work across lines of difference and maintain trust with staff, members, leadership, and external partners.
• Some familiarity with Chicago’s education and political landscape.

Desired Qualifications

• Bilingual
• Experience in a union or collective bargaining environment.
• Experience navigating organizational risk and ensuring compliance with internal policies and external requirements.
• Prior experience in a Chief of Staff or senior advisory role.

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 Chief of Staff is expected to work onsite at CTU Headquarters daily.

Compensation

CTU offers a competitive compensation package including experience based salary (please ensure that all relevant experience is included on your resume) and comprehensive benefits, including the following:

• $153,000
• Employer subsidized medical, dental, and vision insurances 
• 9% Employer Contribution 401(k) 
• 15 PTO Days
• 3 Weeks Vacation Time First Year
• Short Term Disability
• Health Savings Account /Dependent Care Flexible Spending
• Cell Phone Stipend

Our Hiring Timeline and Process

Resumes will be accepted through July 21 (and thereafter on an as needed/ rolling basis until role is filed). An ideal start date would be before or by October 2025.

This search is being supported by NRG Consulting Group. Please contact [email protected] and cc [email protected] with any questions.

We anticipate that our interview process will involve 4 rounds of interviews, ranging in length from 30-60 minutes. Successful candidates that move forward in the hiring process may be invited to complete a skills assessment and will undergo a vetting process, including reference and background check.