Director of Development
Location: Chicago, IL
Job Information:


For Chicagoland youth who desire and deserve more, MetroSquash combines academic support, competitive squash instruction, and enrichment opportunities to empower students to realize their potential and make their mark.

Founded in 2005 serving just 10 students, MetroSquash has grown to serve over 400 Chicago-area teens annually with a $3.0 million budget operating at two sites – Woodlawn and Evanston. In Woodlawn, MetroSquash operates out of a stand-alone center that the organization raised $8 million to construct in 2015. For the time being, our Evanston location operates with a smaller real estate footprint.

To meet a growing demand for its programming, over the next several years, MetroSquash has plans to construct a stand-alone center in Evanston that mirrors the capacity of the Woodlawn facility. By doubling the number of students served to over 800 annually, MetroSquash will be able to better serve the students and families who make our program so special.

MetroSquash is well positioned for growth, as it has emerged from the pandemic in strong fiscal shape and with a vision for the future.  Like other nonprofits that were able to pivot and respond well during the crisis, MetroSquash avoided layoffs, supported its youth and families, raised funds, made time for leadership succession planning, and dedicated itself to organizational quality improvement, all of which laid the groundwork for recruiting new talent and making plans for expansion.


As the economic engine supporting the work of MetroSquash, philanthropy is essential to cover the cost of both its annual high-quality programming and capital investments. MetroSquash raises the funds necessary for its impactful work through a combination of special events, foundation support, and individual contributions. Our organization celebrates our mission and the people who make our work possible through two signature events annually – a spring cup and a fall gala.  We hope to expand our special events programming to include a golf outing this coming year and to continue to grow our base of nearly 2,000 dedicated donors.

Historically, fundraising has been led by the CEO David Kay and the Board of Directors with support from a team of three development staff members. With the addition of a new Director of Development, MetroSquash hopes to build its leadership bench and tap into the deep passion of its current donors, as well as to enlist new supporters to expand the organization’s reach. This is an externally oriented and revenue-generating role; however, the position carries significant management responsibilities. Consequently, the new leader will play a prominent role in shaping and implementing MetroSquash’s fundraising strategy, as well as be integral to the organization’s leadership succession plans.

Reporting to David Kay, the Director of Development will supervise three development positions, and work across teams to advance the MetroSquash mission through philanthropy. The Director of Development will oversee all annual fundraising in addition to the new capital campaign, with support from a team of fundraisers, the Board, and the entire organization. She/he/they will manage and work directly with a portfolio of donors to foster meaningful relationships and creatively leverage opportunities for the organization.

Additional responsibilities include:

Leadership – (25%)

  • Serve as a valued senior leader who interacts with the board, funders, donors, partners, and friends, and is a positive influence on staff across teams
  • Continue to build a culture of philanthropy that is donor-centric and engages students, parents, and staff in the process of stewarding donors
  • Understand the needs and priorities of MetroSquash’s many stakeholders and exhibiting passion for the work that they do

Fundraising and Management – (75%)

  • Oversee an annual fundraising program of $3.0 million generated by three events, individual gifts, corporate/foundation grants, and government support
  • Be responsible for recruiting and managing the fundraising team of three
  • Staff the Development Committee of the Board of Directors and ad hoc committees for the MetroSquash Cup, MetroSquash Gala, and Golf Outing
  • Expand the non-event related individual giving program
  • Oversee online and print marketing and communications materials, including the Annual Report
  • Ensure the necessary systems, records, tracking, reporting and gift acknowledgment processes are in place
  • In collaboration with the CEO and Board of Directors, provide the staff leadership for the anticipated capital campaign to expand in Evanston
  • Oversee an internal readiness plan to ensure adequate staff, information, tools, and processes are in place to support the campaign
  • Create and execute a campaign plan that will provide a successful roadmap for the expanded fundraising effort with support from campaign counsel
  • Carry a portfolio of prospects and regularly meet with donors to tell the MetroSquash story and inspire support for the campaign, and solicit gifts


Our Director of Development will be a professional with at least 7 years’ experience in a nonprofit or business environment and a minimum 3 years in a management role.

Additional skills and attributes of sought-after candidates include:

  • Fundraising experience with a record of success in a reputable organization, nonprofit or after school program.
  • Experience soliciting or staffing the solicitation of five-and six-figure gifts.
  • Campaign experience a plus.
  • Strong strategic thinking and planning skills with an ability to manage concurrent projects and priorities effectively.
  • An able and consistent communicator whose natural leadership abilities and work product will foster collaboration and advance fundraising and MetroSquash overall.
  • Outstanding interpersonal skills; ethical; flexible; adaptable.
  • A passion for increasing access to opportunity in low-income communities and a commitment to the mission and vision of MetroSquash.

To participate in our confidential search process, please send your application (to include both a cover letter and resume) directly for consideration to our recruiting partner Margie DeVine at  Further inquiries or questions?  Call or text Margie on her cell at 773-892-2993.

MetroSquash offers a competitive salary ($100,000 – $120,000) and comprehensive benefits package to include medical, dental, vision, disability, 403b, paid time off, paid company holidays, professional development opportunities and more.  MetroSquash is an Equal Opportunity Employer. Applicants may request any reasonable accommodation that may be necessary to participate in the application process. MetroSquash is located at 6100 S. Cottage Grove Ave, Chicago, IL 60637.  For more information about the organization, please visit: