Managing Director of Development

Application Instructions Click Apply to submit your online application. Please attach a resume and thoughtful cover letter on the "My Experience" page in the "Resume/CV" field. Active City Year Staff members must login to Workday to apply internally. Number of Positions: 1 Work Location: 100% On-Site Position Overview City Year Chicago is seeking a skilled fundraising professional with an entrepreneurial mindset to be the Managing Director of Development. The ideal candidate is an ambitious and sophisticated forward-thinker, communicator, and equity-driven fundraising professional who thrives in roles that require them to be strategic, creative, and collaborative. Reporting to the Executive Director, as a member of the site’s Executive Leadership Team, the Managing Director of Development (MDD) will lead a team of 5 development professionals to manage and implement the fundraising strategy for the Chicago office. This person is responsible for developing and implementing the Development strategy for City Year Chicago to raise and sustain at least $3.75M from the private sector in FY27 and grow annually. The MDD will develop and execute strategic, diversified development plans to raise funds through grant writing, individual giving, and institutional partners, such as corporations and foundations. A focus on establishing multi-year contributions, identifying new funding sources and management of ongoing donors will be expected. The ideal candidate is an initiative-taking problem-solver and strategic thinker who is committed to helping advance educational equity by developing leaders and supporting students in Chicago’s most under-resourced schools. The salary range for this role is $145K - $165K annually, commensurate with experience. Job Description Responsibilities Fundraising Strategy: In partnership with the Executive Director and the City Year Chicago’s Board and Development team, 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. In partnership with the Executive Director, 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. Partner with the Executive Director to 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. Developing strategies to identify new individual supporters, fully leverage existing relationships, increase multi-year commitments, and maintain or elevate current commitments. Develop strategies to 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. People Management & Team Leadership: Hire, lead, and retain a team of 5 development professionals. Directly supervise 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. Relationship Cultivation and Fundraising Management: Build meaningful relationships that result in securing both monetary and in-kind multi-year support for City Year Chicago. Able to grow a transactional relationship into a transformational relationship. Oversee and support Corporate Partnerships and Major Gifts Development fundraising efforts. Serve as a public representative of the organization, including cultivating relationships with community members, including prospective gift givers in order to build awareness of and commitment to City Year Chicago’s work. 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. Manages the identification and cultivation of new corporate and foundation partnerships, as well as the grant proposal and reporting processes for corporate, foundation and government funders. Develop successful identification, cultivation, solicitation and stewardship strategies to direct and monitor the progress of current and future donor relationships. Ensure a disparate and sustainable site donor base. Portfolio Management: Build and manage a portfolio consisting of donors and prospects with $25,000+ capacity for giving, and 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. Document and maintain clear and timely records and call reports to track contacts, donor giving, and notes in the Salesforce database. Board Management and Engagement: In partnership with the Executive Director, the MDD will engage the Board to meet critical financial and advocacy goals for the organization. Participate in quarterly Board of Directors meetings and prepare monthly, quarterly and annual reports as requested by the Executive Director and Board. Serve as primary relationship manager for Development Committee or Development focused board members. Provide regular updates and maintain engagement (both financially and otherwise) to ensure Board retention and satisfaction. Oversee the execution and strategy of the associate board and alumni board to support site fundraising efforts and strategic initiatives Events and Civic Engagement Program Strategy Leadership: In partnership with site leadership and Development team, drive strategies to leverage large-scale fundraising events, including our annual Ripples of Hope Gala as well as smaller events to thoughtfully engage donor communities. Partner with the Managing Director of Partnerships and Civic Engagement to drive the strategy around how to leverage our Civic Engagement efforts to create fundraising and service opportunities for corporate partnerships and individual donors. Marketing and Communications: Experience crafting communication on behalf of others with keen awareness of audience and impact. Ability to manage 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. Experience communicating with both internal and external audiences of varying levels of seniority. Development Operations: In partnership with the Development Operations staff, support development business processes from donor identification through to stewardship, ensuring accurate maintenance of records and donor information in the Salesforce database. Direct monthly pipeline meetings with the Development team and Executive Director to provide updated revenue figures, pipeline reports, and progress towards monthly/quarterly goals. Identify areas for operational improvements and drive continual improvements of processes. Organizational Leadership: Act as a key advisor to the Executive Director and senior leadership in aligning fundraising strategy with the organization’s multi-year site plan, ensuring that philanthropic investments directly support long-term programmatic growth, expansion, and sustainability. Help shape organizational strategy and play a leadership role in implementing the site’s local operating plan as a member of the Executive Leadership Team. Work collaboratively with other site departments and City Year’s national and regional staff. Represent, respect, and role-model City Year’s organizational culture and values internally as a member of the site Senior Leadership Team, and externally as a primary representative of the organization. Actively contribute as leadership team member. Partner with all departments through site events, projects, and cross-departmental committees as needed to ensure site-wide goals are met. Benefits Full-time employees will be eligible for all benefits including vacation, sick days and organization holidays. You may participate in all benefit programs that City Year establishes and makes available to eligible employees, under (and subject to all provisions of) the plan documents that govern those programs. Currently, City Year offers medical, dental, vision, life, accidental death and dismemberment and disability coverage, Flexible Spending Accounts (FSA), and other benefits including 401(k) plan(s) pursuant to the terms and conditions of company policy and the 401(k) plan document. For more information, click here. Employment at City Year is at-will. City Year does not sponsor work authorization visas. City Year’s dual mission is to expand educational opportunity for all students and develop the next generation of leaders through national service. Trained teams of City Year AmeriCorps members provide support to students, classrooms and the whole school. Schools that partner with City Year are up to two to three times more likely to improve in English and math assessments, and the more time students spend with AmeriCorps members, the more they improve on academic, cognitive and interpersonal skills— skills that help students thrive in school, college and career. City Year’s 900 staff and 2,000+ AmeriCorps members work and serve in 29 communities across the U.S., including Boston (where City Year was founded in 1988 and is headquartered), Baton Rouge, Buffalo, Chicago, Cleveland, Columbia, Columbus, Dallas, Denver, Detroit, Jacksonville, Kansas City, Little Rock, Los Angeles, Memphis, Miami, Milwaukee, New Hampshire, New Orleans, New York, Orlando, Philadelphia, Providence, Sacramento, San Antonio, San José/Silicon Valley, Seattle/King County, Tulsa and Washington, D.C. City Year also has international affiliates in the U.K. and South Africa. A proud member of the AmeriCorps national service network, City Year is supported by AmeriCorps, local school districts and private philanthropy. City Year has been designated a 4-star charity by Charity Navigator since 2003, putting City Year in the top 1% of non-profits nationwide for accountability, transparency and responsible fiscal management, and among the most trustworthy nonprofits in America. At City Year, we sometimes say we work not only “at” City Year, but also “on” City Year, recognizing that the organization, like our world, is constantly evolving and changing. Two things that have never changed: our steadfast belief in the power of young people to change our world for the better; and our aspiration to create positive school and work environments where everyone feels a sense of connection, is supported to do their best work, and is able to learn, contribute, lead and create to their fullest potential. 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. Fair Labor Standards Act Family and Medical Leave Act Learn more at www.cityyear.org, City Year’s Facebook page, on X (formerly Twitter), and LinkedIn.