Now Hiring: Volunteer & Outreach Manager

Are you looking for a role where you can make a difference? Are you interested in helping to bridge the educational opportunity gap for Chicago Public School students by providing them with an after-school program that supports their academic, career, and leadership success? If so, consider joining the Chicago Debates team.

For over twenty years, Chicago Debates has partnered with Chicago Public Schools to provide debate programming across its district. Through the transformational activity of debate, students are empowered to find their voice, succeed in college and career, and become community leaders. Chicago Debates administers and supports debate programming in over 90 middle and high schools across the city. As the largest of the 22 urban policy debate leagues in the country, we will support nearly 1800 CPS students in the 2019-2020 school year.

Position Overview

Chicago Debates seeks a mission driven, engaging, enterprising, outgoing, and service-oriented candidate with a demonstrated passion for volunteerism and education to join our team. The Full-Time Volunteer and Outreach Manager will assist us in achieving our mission of advancing the educational achievement, community contributions, and life success of Chicago’s youth through the transformative power of academic debate. The Volunteer and Outreach Manager will work in collaboration with other program staff members and report to the Director of Programs.

Core Responsibilities

  • Principal and primary responsibility for all recruitment, training, and management of volunteers, mainly judges for interscholastic weekend debate tournaments.
  • Use technology to recruit – e-mails, texts, newsletters, Google groups, websites, social media.
  • In-person recruiting at events throughout the city, including volunteer fairs and at area colleges and universities.
  • Train all volunteers to become debate judges or tournament volunteers.
  • Thank volunteers after events and securing future volunteer commitments.
  • Train highly active volunteers to take leadership as judge table operators or recruiters/trainers.
  • Prepare non-debaters for a challenging volunteer experience as debate judges, with debrief and follow-up training.
  • Manage background checks (online and/or fingerprinting) for every volunteer and follow-up with ineligible individuals.
  • Create all onboarding and training materials for volunteers, including handbooks, Powerpoint trainings, Prezis, video or podcast tutorials, etc.
  • Manage judge table at tournaments, including pre-tournament preparation and on-site tournament event management (average 2 weekends a month from October – April).
  • Assist program staff with all tournament preparation work, including photocopying and sorting and transporting supplies, awards, and T-shirts.
  • Directly manage judge table operators and contract staff and assign them to help run tournaments.
  • Track, pay, and following up with all paid volunteers and tournament staff, under supervision of Program Director and financial staff.
  • Assist the Program Director and other Chicago Debates staff in tournament and volunteer record-keeping, payments, and budgeting.
  • Gather, update, and organize all volunteer data in a responsible manner and take lead in tracking and reporting.
  • Continuously update databases, contact info, and any rosters/spreadsheets tracking student and judge participation.
  • Design, compile, and deliver program and volunteer survey data.
  • Use data to improve our volunteer experience and onboarding/retention.

Represent Chicago Debates in the community, including:

  • Assist in the preparation and delivery of special debate events, including events held by sponsors at law firms or corporations; public events and fundraisers; conferences, etc.
  • Assist in the design and delivery of events to motivate and recognize students, teachers, and judges.
  • Work with the Development and Communications Manager in managing the Volunteer Committee of the Associate Board.
  • Train and manage judges at corporate-sponsored debate events, including events connected to members of the Board of Directors.
  • Communicate with instructors and school staff about service learning hours and class credit and certifying volunteer hours.
  • Provide ongoing reporting on number of volunteers for each event and set targets and timelines, working with all program staff.
  • Managing office interns, including CPS summer student interns and short-term college student interns during the summer or an academic term.
  • Other duties as assigned.

Work Schedule

Full-Time, Monday through Friday, 10:00am-6:00pm with an expected work week of 40-50 hours. Ability to work remotely one day a week.

This position includes some evening and weekend work during the tournament season from October – April (average three evenings a month & two Saturday’s a month). These dates are identified in advance in our calendar. Comp time is offered for weekend work, with some stipulations.


Range $50k-$60k. Final salary to be determined based on experience and skills. Full-time employees are eligible for health, dental, and vision insurance, Retirement, PTO, Professional Development Allowance, Sick Days, and Holidays. Chicago Debates is seeking a commitment of at least two years.

To Apply

Submit a cover letter, resume, and salary requirements to

Chicago Debates is an equal opportunity employer.

Qualifications and Requirements

  • Bachelor’s degree required.
  • At least 3-5 years of experience in a role involving the recruitment, training, and management of volunteers, preferably for a large-scale program.
  • Demonstrated ability to deliver high-quality and engaging trainings.
  • Demonstrated ability to train a variety of learners, including adult volunteers with little or no debate experience.
  • Experience in urban education a plus, specifically Chicago Public Schools.
  • Experience designing and delivering large-scale, time-sensitive events involving hundreds of volunteers highly desirable.
  • Must have ability to prioritize multiple assignments; work independently; communicate about challenges; plan; and most importantly, follow through.
  • High level of experience using volunteer databases and CRM software required (Volgistics, Raiser’s Edge, Neon, Salesforce, etc.).
  • Advanced computer skills in Google Suite (Gmail, Google calendar, Google forms and Google Drive) and Microsoft Suite (Word, Excel, Powerpoint and their Google Docs equivalents).
  • Previous debate experience not required, but a plus, as either a coach, administrator or as a student competitor, especially in urban debate.
  • Valid driver’s license and clean driving record required.
  • Daily access to a reliable vehicle for work is required.
  • Legal clearance to work with minors. Must pass a background check, TB test, and any others required by Chicago Public Schools (potentially including a drug test).
  • trong ethics, maturity, and appropriate boundaries for adult interactions with minors, including compliance with all Chicago Public Schools HR and reporting requirements.
  • Must be available to work some evenings and weekends during the tournament season from October – April (average three evenings a month & two Saturday’s a month).
  • Physical demands include carrying supplies (boxes up to 50 pounds, paper, printers, computer, t-shirts, food, etc.) for tournaments and teams from your car to a variety of school and event locations.


  • Strong connection to the Chicago Debates mission.
  • Empathy, humility, flexibility and willingness to serve and lead volunteers and tournament staff in an often-challenging and fast-changing urban education setting.
  • Enterprising, outgoing communication style that draws people to our mission.
  • Eagerness to go out to sites (colleges, volunteer fairs, corporations) to recruit and train judges.
  • Ability to prioritize multiple events and volunteer goals at once – highly organized approach to planning and reporting.
  • Positive, solution-oriented approach in a team working toward common goals.
  • Strong cultural competency operating in a diverse population with a variety of needs and challenges and communication styles.
  • Strong interpersonal, verbal and written communication skills.
  • A self-starter, creative, and forward thinker.
  • Strong work and financial ethics.
  • Kindness, discretion, and patience in helping volunteers with problems involving their payment, service learning, or academic credits.
  • Must have the utmost integrity and an ability to process, protect and exercise discretion in handling confidential information and materials.
  • Professional and ethical commitment to student protection and student privacy.


Additional Salary Information: Range $50k-$60k. Final salary to be determined based on experience and skills. Full-time employees are eligible for health, dental, and vision insurance, Retirement, PTO, Professional Development Allowance, Sick Days, and Holidays. Chicago Debates is seeking a commitment of at least two years.
Internal Number: 3123003445