Now Hiring: Director of Development

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

The Director of Development (DOD) will be responsible for crafting and executing an annual comprehensive fundraising plan that ensures Chicago Debates has the resources necessary to fulfill our mission and meet our strategic priorities. In partnership with two direct reports, provide strategic leadership in order to diversify, strengthen and double Chicago Debates’ $1.3MM budget by FY24 with a focus on individual, corporate, and foundation giving. The ideal candidate will have a track record of demonstrated success in fundraising that includes: plan writing and metrics tracking; prospecting, direct stewardship and direct solicitation; supporting others in stewardship and solicitation; cross-team project management such as producing grant proposals/reports, donor communications, and annual reports; and management of direct reports and consultants.

Organization’s financial resources come from:

  • 26% Fundraising Events
  • 22% Public Funding
  • 20% Foundations
  • 14% Individuals
  • 14% Corporations
  • 4% Other

Core Responsibilities

The DOD will work with the Executive Director to lead Chicago Debates’ fundraising priorities and strategies with the goal of increasing visibility, funding, donors, and donor retention. The DOD will identify, grow, and strengthen relationships in order to expand Chicago Debates’ presence and generate funding. Responsibilities include but are not limited to the following:

Overall Fund Development

  • Assess short- and long-range funding needs with staff and develop and implement the overall fundraising strategy and work plan to meet those needs.
  • Develop annual fundraising goals and objectives, specifying amounts to be raised from individuals, corporate and foundation support, and other constituencies.
  • Review and analyze past campaigns and pertinent factors in developing fundraising goals.
  • Expand funding by identifying prospective foundation, corporate and individual donors, developing strategies to cultivate those relationships and solicit donations.
  • Lead fundraising strategies by crafting proposals, writing presentations, coordinating stewardship visits/meetings, managing logistics, and strategic communications.
  • Engage foundations, corporate, individual donors, and other stakeholders on a continual basis to establish and maintain communications and relationships with them.
  • Oversee the development of solicitation materials related to fundraising in collaboration with the Communications and Engagement Manager.
  • Work with the Executive Director to prepare and manage relevant areas of the budget and ensure compliance with funding source guidelines and deadlines.
  • Ensure timely and accurate reporting to funders.
  • Create monthly reports that reflect activities and progress in meeting fundraising goals.
  • Oversee the CRM process, including ensuring the validity of all data in the fundraising database and tracking systems.
  • Work collaboratively across teams, providing leadership, input, and ideas to enhance Chicago Debates and its projects.

Donor and Stakeholder Engagement

  • Serve as a creative thought leader on how to advance Chicago Debates’ relevance to and engagement of new audiences.
  • Research, identify, qualify, cultivate, and steward relationships with existing and prospective donors, establishing portfolios of current and potential donors.
  • Oversee donor communications that support the fundraising program and engagement and stewardship of donors, including fundraising collateral, acknowledgements, recognition, newsletters, specialized emails, etc.
  • Develop, promote, and manage programming to donor engagement opportunities to cultivate and solicit support from current and potential donors (e.g. Tournament Tours, Cocktail Receptions, etc.).
  • Manage the planning and execution of all mail and email appeal campaigns.
  • Utilize data and evaluative measures to assess donor satisfaction, identify improvements, and implement modifications.

Board and Staff Engagement

  • In conjunction with the Executive Director, provide leadership support to the Board of Directors to build a broad base of financial support for the organization’s long term fundraising efforts, such as Board Giving campaigns, communications, outreach and follow-up, engagement opportunities, etc.
  • Work closely with the Executive Director and Board(s) to strengthen existing corporate and individual relationships and establish new ones.
  • Revive and lead the Fundraising Committee of the Board to support the overall fundraising goals.
  • Take leadership in providing the tools, resources, schedules and reminders for the Executive Director and Development Team to execute on fundraising strategies and tasks.
  • Prepare the Executive Director and Board members for gift solicitations, accompany on calls as needed and provide appropriate follow-up.
  • Assist in the prospecting of new board members and participate in the board orientation process.
  • Manage the engagement of the Associate Board (AB), which may include staffing quarterly committee meetings, management of 1-2 AB events per year, engage and organize AB members to support organizational events and fundraising needs, and recruitment of new AB members.

Special Events

  • Lead, plan, manage and evaluate fundraising events, especially the annual Make Room for Debate luncheon.
  • Identify, solicit, and secure sponsorships and ticket sales to achieve event fundraising goal.
  • Ensure early sponsorship materials
  • Day of event Programming, including speakers and student ambassadors.
  • Secure venue and contractors.
  • Work closely with Board of Directors to secure early sponsorships
  • Lead the process to identify and secure event honoree and Co-chairs.
  • Provide oversight and management for AB Fundraising events.

Team Management

  • Build and cultivate a high performing, professional and dedicated development team with two direct reports.
  • Lead the development team to implement fundraising plans that outline monetary and activity goals targeting all donor levels and for all areas of support.


  • High degree of commitment and passion for the mission of Chicago Debates.
  • Alignment with organizational values.
  • Ability to work in a fast-paced environment.
  • Creative, self-starter attitude, with the desire to get out of the office and build external relationships.
  • Ability to take initiative and work both collaboratively and independently.
  • Ability to engage with diverse audiences, including donors, board members, students, coaches, volunteers, staff, executives, etc.
  • Professional presence. Position requires the utmost integrity, ethical behavior, and appropriate business practices.
  • Commitment to advancing as a professional in nonprofit development.

Work Schedule

Full-Time, Monday through Friday, 9:00am-5:00pm and requires 40-50 hours per week with occasional evenings and weekends. Ability to work remotely one day a week.


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 Dr. Toinette Gunn, Executive Director at Cover letters without salary requirements will not be considered.

Chicago Debates is an equal opportunity employer.


  • Bachelor’s degree required. Advanced degree preferred.
  • 6+ years of nonprofit fundraising experience. Certified Fund Raising Executive Preferred.
  • Deep understanding of fundraising, including basic selling skills, proper stewardship, individual giving strategies, tools, and resources, and various approaches to generating revenue.
  • Demonstrated record of successful solicitation of five & six figure donations, from identification of prospects through stewardship and closing.
  • Knowledge of the Chicago philanthropic community is required with existing relationships with foundations and corporations.
  • Ability to solicit and grow relationships with corporations, foundations, and major donors.
  • Experience in researching and writing grants with deep knowledge in research databases and best practices.
  • Exceptional organizational skills, with detail orientation.
  • Ability to manage multiple projects simultaneously from start to completion.
  • Strong written, verbal, and interpersonal communication skills, including sentence and paragraph construction, proper grammar and spelling, concise and professional writing, and public speaking and persuasiveness.
  • Proficiency with core social media platforms (e.g. LinkedIn, Facebook, Twitter, IG, etc.) and ability to utilize them as a tool in identifying and expanding donors.
  • Advanced computer skills including use of Word, Excel, PowerPoint, and NEON or other CRM fundraising software and tools.
  • Remain abreast of fundraising trends and the nonprofit community


Additional Salary Information: 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