Senior Director, Development

Position Overview The Senior Director of Development is responsible for executing the strategy to raise and sustain 1.85million private revenue and grow annually. Reporting to the Executive Director and serving as a member of the Senior Leadership Team, the Senior Director of Development supports the site's private-sector fundraising efforts through diversified strategies that include individual giving, major gifts, corporate partnerships, foundation grants, and signature events. The Senior Director of Development leads key fundraising efforts, and works in close partnership with the Managing Director of Development Executive Director, Board, and colleagues across departments to meet annual fundraising goals and grow revenue over time. The ideal candidate is a strategic, action-oriented leader and relationship builder who inspires donors and partners to invest in our mission of advancing educational opportunity through national service. Success in this role requires strong day-to-day follow-through, sound judgment, and systems discipline, in addition to setting fundraising direction. Job Description Minimum Qualifications 5+ years of progressive fundraising experience or comparable relationship management experience, demonstrating readiness to independently own complex portfolios and processes Authorized documentation to work in the United States of America Criminal background history clearance to work with school-age children, depending on the position Responsibilities Fundraising Strategy & Execution Support in execution of our comprehensive, site-specific fundraising strategy, aligned with City Year’s enterprise direction, to meet or exceed annual revenue goals 1.85 and position the organization for long-term growth. Inspire, cultivate, solicit, and steward donors through personalized engagement with an emphasis on major gifts and multi-year commitments. Develop and deepen institutional partnerships with corporations and foundations to secure and sustain significant support, including stewardship and growth of Team Sponsors at the $100,000+ level Collaborate with the national Development team to steward and deliver on multi-site and national partnerships. Oversee the development of compelling grant proposals and ensure timely, accurate funder reporting. Monitor and report on revenue performance and pipeline health; use data insights to identify process improvements and optimize fundraising strategies. Portfolio Management Build and manage a portfolio with a personal revenue target of $750,000, consisting of donors and prospects with $25,000+ giving capacity, including prospects with $100,000+ potential. Conduct 75+ meaningful donor engagements annually, including meetings, calls, and stewardship touchpoints Maintain accurate, timely donor records, call reports, and moves-management updates in Salesforce, using CRM data to prioritize work, identify barriers, and inform next steps. Team Leadership & Collaboration Serve as the one of the primary fundraiser for the site, while equipping other site staff with tools and strategies to support fundraising efforts. Partner closely with Impact staff and AmeriCorps members to connect fundraising efforts with program priorities and elevate the authentic impact of City Year’s work. Serve as a senior leader of the site by fostering team collaboration and belonging and contributing to site-wide goals. Role models a growth mindset and commitment to City Year’s culture and values. Performs additional responsibilities as assigned by the direct supervisor to advance City Year’s mission. Board Engagement Partner with the Executive Director to engage the Board in fundraising and advocacy efforts. Serve as primary staff liaison to the Associate Board. Support strategies to achieve 100% board giving and increase board-led prospecting and stewardship. Events Leadership Oversee strategy and execution for signature fundraising events (e.g., gala, community breakfasts, service days) to drive donor engagement and revenue generation. Ensure events are mission-centered, well-produced, and effective in advancing donor cultivation goals. Marketing, Communications & Community Engagement Oversee marketing and branding strategy, including promotional materials, web content, and donor communications Represent City Year at external events and community engagements to elevate visibility and build new relationships. Preferred Qualifications Experience building or leading a diversified fundraising program or comparable relationship-management strategies (e.g., individual giving, major gifts, foundations, corporate partnerships, or similarly complex stakeholder portfolios) Proven track record of securing major gifts and institutional funding Experience managing a team or leading cross-functional initiatives Excellent written and verbal communication skills, including persuasive writing and presentations tailored to external partners (e.g., donors, funders, or senior stakeholders) Comfort representing the organization publicly with donors, civic leaders, and corporate partners Proficiency in CRM systems (Salesforce preferred) and Microsoft Office Suite City Year/AmeriCorps experience a plus Strong fundraisers come from many paths; we value transferable relationship-building experience and encourage candidates with varied backgrounds to apply. Competencies Project Management: Plans, organizes, and manages complex fundraising initiatives and events to ensure timely, high-quality execution. Decision-Making: Uses data and qualitative insights to make informed decisions, anticipate challenges, remove barriers to progress, and escalates issues when appropriate to keep work moving forward. Understanding & Building Connection: Cultivates trust-based, meaningful relationships with donors, board members, partners, and staff to strengthen organizational support. Strategic Thinking: Develops and implements multi-year strategies to drive revenue, translating them into clear priorities, systems, and sustained execution. Collaboration: Works effectively across teams; builds shared purpose and alignment; models inclusive, mission-centered leadership. Physical requirements Ability to sit for extended periods and occasionally stand or walk Manual dexterity for typing, writing, and handling office equipment Visual acuity to read screens and printed materials Hearing ability to participate in conversations and respond to phone calls Occasional lifting of items up to 10–20 lbs (e.g., event materials) Working Conditions In-person In Milwaukee Operates in a professional office environment using standard office equipment Requires regular local travel to donor meetings, events, and community engagements Typical schedule: Monday–Friday, 8 am – 5 pm, with occasional evening or weekend commitments Requires a valid driver’s license for travel as part of job duties. Must have reliable internet access for hybrid work Noise level generally moderate Working at City Year City Year Benefits City Year offers a comprehensive benefits package that helps our employees live their best lives and grow personally and professionally. Compensation (70,000- 85,000) Employment at City Year is at-will. City Year does not sponsor work authorization visas. 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 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. 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 City Year’s Facebook page, on X (formerly Twitter), and LinkedIn. #J-18808-Ljbffr City Year