VP, Development - Midwest

City Year • Chicago, IL

9d • $170,000 - $190,000 • Hybrid

About The Position

City Year is seeking a VP, Development - Midwest to lead, grow, and sustain philanthropic partnerships across the region, with a 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 for individual, family, and institutional giving while expanding business development efforts and strengthening City Year’s regional brand and visibility.

The role works closely with the national Revenue & Growth team, local Executive Directors, Site Boards, national foundation and corporate teams, and other leaders to increase philanthropic investment in City Year’s work. The position is hybrid, requires the VP to be based in Chicago and work from the local site office two to four times per week depending on travel and meetings, and involves approximately 60% travel across the Midwest and larger region and to national convenings.

The VP leads regional major-gifts strategy and relationship development, builds donor pipelines, and supports local fundraising capacity and systems. The role also develops regional stewardship and engagement strategies, represents City Year at external events, and works with Marketing and Communications to adapt messaging and storytelling for regional audiences. Success includes growing the regional major-gifts pipeline and supporting a $2 million annual goal, achieving fundraising priorities, and expanding regional visibility and donor engagement.

Requirements

• Bachelor’s degree or equivalent combination of education and experience.
• At least 8 years of relevant experience in fundraising, business development, nonprofit leadership, or related advancement roles.
• Demonstrated success securing major gifts at the $100,000+ level and managing a portfolio of high-net-worth individuals and/or institutional donors.
• Proven ability to identify and engage new donors, design cultivation experiences, and grow a top-of-funnel pipeline.
• Excellent communication, strategy, relationship, and project management skills.
• Experience using CRM platforms to manage pipelines, forecasting, and donor insights.
• Willingness and ability to travel across the Midwest and larger region and to national convenings, approximately 60%.
• Must be based in Chicago and work from the local site office two to four times per week, depending on travel and meetings.

Nice To Haves

• Familiarity with philanthropic networks in the region; strong relationships are preferred.
• 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.

Responsibilities

• Serve as lead strategist and relationship manager for a portfolio of individual donors, corporate partners, and family foundations with capacity for transformational 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 using regional networks, corporate champions, and cross-sector partnerships.
• Conceptualize and execute cultivation and thought leadership events to introduce prospects to City Year’s work and deepen existing supporter engagement.
• Collaborate with national major-gifts, communications, foundation, and corporate teams to position the Midwest as a strategic priority region.
• Partner with national Individual Giving and Development teams to align local strategies with organizational goals.
• Support, coach, and advise local development staff and site leadership on fundraising best practices, moves management, and donor engagement.
• Optimize systems, workflows, and tools, including Salesforce, dashboards, and calendars, to support donor cultivation, stewardship, and forecasting.
• Design and lead a year-round regional stewardship and engagement strategy based on local impact moments and national campaigns.
• Represent City Year at regional convenings, donor events, and other external opportunities to elevate visibility and build partnerships.
• Work with Marketing and Communications to tailor national messaging for local audiences and deploy regionally relevant content and storytelling tools.
• Advance City Year’s digital storytelling and regional thought leadership to inspire philanthropic engagement.

Benefits

• Vacation, sick days, and organization holidays.
• Medical, dental, vision, life, accidental death and dismemberment, and disability coverage.
• Flexible Spending Accounts (FSA).
• 401(k) plan(s).
• Other benefit programs made available to eligible employees, subject to applicable plan documents and company policy.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive