Managing Director of Development

Position Overview City Year Chicago is seeking a skilled fundraising professional with an entrepreneurial mindset to serve as the Managing Director of Development (MDD). The MDD will lead a team of five development professionals and work with the Executive Director and the Board to develop and implement a fundraising strategy that will raise and sustain at least $3.75M from the private sector in FY27, with a growth target for the following years. This role requires a strategic, creative, and collaborative leader who is equity‑driven and capable of managing grant writing, individual giving, and institutional partnerships, with a focus on multi‑year contributions, new funding sources, and ongoing donor stewardship. Responsibilities Leverage and enhance the site’s existing Development plan to implement a strategic and diversified fundraising plan that meets the current goal of raising $3.75M from the private sector and anticipates future needs and growth objectives. Develop, implement and monitor short‑ and long‑term fundraising strategies aligned with the organization’s multi‑year site plan, translating organizational vision and programmatic priorities into actionable, multi‑year plans that support sustainable growth and measurable impact, with a goal of reaching $6M in annual fundraising. Develop and execute a tailored fundraising and engagement strategy for the Executive Director’s portfolio, ensuring effective cultivation, solicitation, and stewardship of high‑priority donors and prospects. Collaborate with leadership to translate organizational vision into actionable fundraising initiatives, ensuring sustainability, scalability, and measurable impact over time. Identify new individual supporters, fully leverage existing relationships, increase multi‑year commitments, and maintain or elevate current commitments. Identify and secure partnerships with corporations and foundations that reflect their marketing and business needs as well as philanthropic and community engagement goals. Implement a high‑quality stewardship program that engages, recognizes, and thanks supporters to strengthen their relationship with the organization. Hire, lead, and retain a team of five development professionals, directly supervising the Director of Corporate Partnerships, Director of Individual Giving, Director of Foundations and Grants, and the Senior Manager of Development Operations. Support ongoing coaching, career growth, and professional development for department staff. Build meaningful relationships that result in securing both monetary and in‑kind multi‑year support for City Year Chicago, growing transactional relationships into transformational ones. Oversee and support Corporate Partnerships and Major Gifts Development fundraising efforts, and serve as a public representative of the organization. Maintain oversight over all fundraising activities including major giving, grants, special events, direct mail appeals, corporate partnership initiatives. Manage relationships and communication with current corporate and foundation funders; manage the identification and cultivation of new partnerships, as well as the grant proposal and reporting processes. Develop successful identification, cultivation, solicitation and stewardship strategies to direct and monitor the progress of current and future donor relationships. Build and manage a portfolio of donors and prospects with $25,000+ capacity for giving, with a focus on prospects capable of giving $100,000+; cultivate, solicit, and close annual, major gift and multi‑year contributions. Achieve 75 meaningful contacts with portfolio prospects annually and make 50 intentional asks, documenting and maintaining clear and timely records in Salesforce. Engage the Board to meet critical financial and advocacy goals, participate in quarterly Board of Directors meetings, prepare quarterly and annual reports, and manage Development Committee or Development‑focused board members. Oversee the execution and strategy of the associate board and alumni board to support site fundraising efforts. Drive strategies to leverage large‑scale fundraising events, including the annual Ripples of Hope Gala, and smaller events to engage donor communities. Partner with the Managing Director of Partnerships and Civic Engagement to leverage civic engagement efforts to create fundraising and service opportunities. Develop and execute compelling communication tools that drive people to support and champion City Year Chicago, including press releases, media advisories, social media communication and marketing events. Support development business processes from donor identification through to stewardship, maintain accurate donor information in Salesforce, and drive continuous operational improvements. Act as a key advisor to the Executive Director and senior leadership in aligning fundraising strategy with the organization’s multi‑year site plan, shaping organizational strategy, and representing the organization externally. Benefits Full‑time employees are eligible for vacation, sick days, and organization holidays. Participation in medical, dental, vision, life, accidental death and dismemberment, disability coverage, Flexible Spending Accounts (FSA), and 401(k) plans as per company policy. Employees may participate in all benefit programs established by City Year. Employment is at‑will; City Year does not sponsor work authorization visas. As an equal opportunity employer, City Year is committed to providing employment opportunities to all qualified individuals and does not discriminate on the basis of race, color, ethnicity, religion, sex, gender, gender identity and expression, sexual orientation, national origin, disability, age, marital status, veteran status, pregnancy, parental status, genetic information or characteristics, or any other basis prohibited by applicable law. #J-18808-Ljbffr