Our Schools Action Chicago: Operations Director

Our Schools Action Chicago:
Operations Director LOCATION

Chicago, IL

$6000 - $7000 (Monthly)

Managed a budget of $100,000, Managed a budget of $1,000,000

Our Schools Action Chicago

Operations

PAC

Director (overseeing a department. Ex: Political Director, Communications Director)

Please submit your application on the google form before June 12th.

Reports To: OSA Campaign Manager

Position Type: Full-Time, Exempt

Location: Chicago, IL

Organization: Our Schools Action Chicago

Summary

The Operations Director serves as the organizational backbone of the Our Schools Action Chicago campaign. Reporting to the Campaign Manager, this role is responsible for building and maintaining the systems, structures, and processes that enable a high-performing, multi-district electoral campaign. The Operations Director will oversee recruitment, staffing, budget management, compliance, and day-to-day logistics, ensuring that all campaign arms function cohesively and efficiently.

Organization Overview

This year, Chicagoans have the opportunity to elect their representatives on the 21 member Chicago Public Schools Board of Education. We have a chance to make history by electing a progressive slate of candidates endorsed by a coalition of community, political and labor organizations dedicated to a just and equitable education system. Our Schools Action Chicago is committed to a vision of an education system where every student in Chicago - regardless of their race, income, or zip code receives access to fully resourced, equitable, safe, and healthy public schools.

Position Responsibilities

• Lead all recruitment, hiring, and onboarding processes for campaign staff across all roles.
• Manage and support the full campaign team by setting clear goals, maintaining regular communication, and establishing operational protocols and procedures.
• Oversee back-office functions including payroll administration, budget tracking and oversight, and vendor management.
• Maintain clean, compliant, and up-to-date files for all candidates and political committees.
• Serve as the primary backstop for logistical, administrative, and functional issues across the campaign.
• Manage conflict resolution processes and foster a healthy, accountable team culture.
• Coordinate closely with the CTU Political Team to align campaign operations with broader organizational strategy.
• Ensure compliance with all relevant campaign finance laws and electoral regulations.
• Oversee contracts and relationships with vendors and external consultants.
• Develop and implement systems to track campaign milestones, deliverables, and team performance.

Primary Knowledge,

Skills and Abilities

• Minimum of five years of experience in campaign operations, political organizing, or nonprofit management.
• Demonstrated experience managing large, diverse teams in fast-paced environments.
• Strong background in budget management, payroll, and financial oversight.
• Exceptional organizational skills with meticulous attention to detail.
• Ability to manage multiple competing priorities and meet deadlines under pressure.
• Strong interpersonal and conflict-resolution skills.
• Familiarity with campaign compliance and finance reporting requirements.
• Proficiency with project management tools and platforms.

Secondary Knowledge,

Skills and Abilities

• Prior experience working within a union or labor organization.
• Background in Chicago-area education or electoral politics.
• Experience managing multi-district or multi-site campaigns.
• Familiarity with voter contact and field organizing tools (e.g., VAN, Hustle).

Salary Range: $6,000-7,000/month, commensurate with experience

Duration: Through November 2026, with potential to extend through March 2027

Application Process:

• Fill out this form  by Friday, June 12th
• Screening/first round interview
• Second round interview
• Reference Checks
• Anticipated start date: ASAP or by July 1st