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 hybrid position, the VP must be Chicago-based and in the local site office 2-4x a week (depending on travel and meetings)

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 - $190,000 Annually - Commensurate with Experience and Location

Benefits