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
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.
People Management & Team Leadership:
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:
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.
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.
Board Management and Engagement:
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.
Marketing and Communications:
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.
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.
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.
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.
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.
