VP, Development - Midwest

City Year•Chicago, IL

2d•Hybrid

About The Position

City Year is seeking a VP, Development - Midwest to lead, grow, and sustain philanthropic partnerships across the region. 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 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 based in Chicago and is hybrid, with the VP expected to work in the local site office two to four times a week depending on travel and meetings. Travel across the Midwest and larger region, and to national convenings, is approximately 60%. The VP leads regional major gifts strategy and relationship development, supports local fundraising, and secures transformational philanthropic investments. The role includes managing donor and partner relationships, building a pipeline of new prospects, coordinating cultivation and stewardship, advising local staff and site leadership, and representing City Year at regional events. Compensation is $170,000–$190,000 annually, commensurate with experience and location. Full-time employees are eligible for City Year benefits. Employment is at-will, and City Year does not sponsor work authorization visas.

Requirements

Bachelor’s degree or an 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-plus level and managing a portfolio of high-net-worth individuals and/or institutional donors.
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.
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%.
Must be based in Chicago and work in the local site office two to four times a week, depending on travel and meetings.

Nice To Haves

Strong relationships and familiarity with philanthropic networks in the region.
Experience working within complex national organizations across national and local teams.
Strong 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

Lead regional major-gifts strategy and relationship development to advance City Year’s mission and secure philanthropic investments across the Midwest.
Manage a portfolio of individual donors, corporate partners, and family foundations capable of transformational investments.
Partner with Executive Directors, sites, and national teams to develop and execute fundraising plans focused on long-term growth, major gifts, and new donor acquisition.
Identify and engage prospective supporters, building a top-of-funnel pipeline through regional networks, corporate champions, and cross-sector partnerships.
Create and deliver cultivation and thought-leadership events to introduce prospects to City Year and deepen existing supporter engagement.
Collaborate with national major gifts, communications, foundation, and corporate teams to position the Midwest as a strategic priority.
Align local strategies with broader organizational goals in partnership with national Individual Giving and Development teams.
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, for donor cultivation, stewardship, and forecasting.
Design and lead a year-round regional stewardship and engagement strategy grounded in local impact moments and national campaigns.
Represent City Year at regional convenings, donor events, and other external opportunities to increase visibility and develop partnerships.
Work with Marketing and Communications to tailor national messaging to local audiences and deploy regionally relevant content and storytelling tools.
Advance City Year’s digital storytelling and thought-leadership presence in the region to inspire philanthropic engagement.
Travel across the Midwest and larger region, and to national convenings, approximately 60% of the time.