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…