VP, Development - Midwest

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Number of Positions: 1 Position Overview City Year is seeking a VP, Development - Midwest to help fuel the next chapter of our mission-driven work across the region. This leader will lead, grow, and sustain philanthropic partnerships, with a particular focus on major gifts, new donor acquisition, and strategic regional positioning. The VP will serve as the chief architect and driver of a multi-year growth plan focused on individual, family, and institutional giving, while expanding top-of-funnel business development efforts and strengthening City Year’s regional brand and visibility. This leader will work in close partnership with the national Revenue & Growth team, local Executive Directors, Site Boards, national foundation and corporate teams, and broader leadership to increase philanthropic investment in City Year’s work. In the Midwest, City Year partners with schools and districts across the region, advancing student success while developing the leadership pipeline of future educators and change-makers. This is an exciting time at City Year and a powerful opportunity for a proven fundraiser and people leader to drive sustainable revenue growth in one of City Year’s most dynamic regions. The ideal candidate will be energized by deepening current partnerships, catalyzing new ones, and using strategic engagement, digital storytelling, and high-touch cultivation experiences to inspire greater investment in students, schools, and communities.

Location: This is a remote position, the VP must be based in a Midwest city where City Year operates a site. Job Description Minimum Qualifications Bachelor’s degree or equivalent combination of education and experience Minimum 8 years of relevant experience, with a strong record in fundraising, business development, nonprofit leadership, or related advancement roles Demonstrated success securing major gifts at the $100K+ level and managing a portfolio of high-net-worth individuals and/or institutional donors Proven ability to identify and engage new donors, design compelling cultivation experiences, and grow a top-of-funnel pipeline Excellent communication, strategy, relationship, and project management skills Familiarity with philanthropic networks in the region, with strong relationships preferred Experience using CRM platforms to manage pipeline, forecasting, and donor insights Willingness and ability to travel across the Midwest and larger region, and to national convenings, approximately 60% Willingness and ability to travel across the Midwest and larger region, and to national convenings, approximately 60% Responsibilities The VP will lead regional major gifts strategy and relationship development to advance City Year’s mission, strengthen local fundraising, and secure transformational philanthropic investments across the Midwest. This role is ideal for a strategic, relationship-centered leader who is excited to build momentum, connect supporters to impact, and rally new champions for City Year’s work. Lead and Grow Philanthropic Revenue Serve as the lead strategist and relationship manager for a portfolio of individual donors, corporate partners, and family foundations with the capacity to make transformational or “big bet” six-, seven-, and eight-figure investments Partner with Executive Directors, sites, and national teams to develop and execute a fundraising plan focused on long-term growth, major gifts, and new donor acquisition Identify and engage prospective supporters by building a robust top-of-funnel pipeline, leveraging regional networks, corporate champions, and cross-sector partnerships Conceptualize and execute intimate cultivation and thought leadership events to introduce new prospects to City Year’s work and deepen engagement with existing supporters Collaborate with national major gifts, communications, foundation, and corporate teams to position the Midwest as a strategic priority region within City Year’s national portfolio Strengthen Internal Strategy, Capacity, and Systems Partner with City Year’s national Individual Giving and Development teams to align local strategies with broader organizational goals Support, coach, and advise local development staff and site leadership on fundraising best practices, moves management, and donor engagement Ensure systems, workflows, and tools, including Salesforce, dashboards, and calendars, are optimized to support donor cultivation, stewardship, and forecasting Drive Donor Stewardship, Visibility, and Regional Engagement Design and lead a year-round regional stewardship and engagement strategy anchored in local impact moments and national campaigns Represent City Year at regional convenings, donor events, and other external opportunities to elevate visibility and build strategic partnerships Work with Marketing and Communications to tailor City Year’s national messaging for local audiences and deploy regionally relevant content and storytelling tools Advance City Year’s digital storytelling and thought leadership presence in the region through compelling content that inspires philanthropic engagement Preferred Qualifications Experience working within complex national organizations across national and local teams Strong regional relationships and familiarity with philanthropic, civic, corporate, and cross-sector networks in the Midwest Experience building and activating Board, executive, and volunteer relationships in support of major gift strategy Success designing donor cultivation experiences, thought leadership events, and high-touch stewardship strategies Strong commitment to diversity, equity, inclusion, and belonging, and an asset-based approach to fundraising and community engagement

Competencies Strategic Thinking: Identifies multiple pathways to address complex and evolving fundraising opportunities; anticipates barriers and opportunities; develops plans that align donor strategy with City Year’s mission and priorities

Understanding & Building Connection: Considers the perspectives of others and cultivates trusted relationships with donors, funders, senior leaders, colleagues, and external stakeholders

Collaboration: Connects with stakeholders to identify shared interests and partners across teams to incorporate different perspectives toward a common goal Decision-Making: Uses appropriate context, data, donor insights, and sound judgment to make timely decisions in complex cultivation, solicitation, and partnership opportunities

Project Management: Organizes, prioritizes, tracks, and manages donor strategies, proposal development, engagement, and follow-through to support high-quality execution

Accountability: Holds self accountable for actions, follow-through, fundraising progress, and impact on team, revenue goals, and the broader organizational mission Success Measures Growth of a robust regional major gifts pipeline and $2M annual goal, including new donor prospects and six- and seven-figure opportunities Achievement of annual and multi-year fundraising priorities across the Midwest region Successful cultivation, solicitation, and stewardship of individual, family, corporate, and institutional funders Expanded regional visibility, donor engagement, and strategic positioning for City Year’s work in the Midwest Compensation $170,000 Annually - Commensurate with Experience and Location 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.