The Opportunity: After School Matters seeks a dynamic and strategic Chief Development Officer (CDO) to lead and advance a comprehensive fundraising program that generates approximately $10 million annually in private revenue.
As a key member of the executive leadership team, the CDO will shape the organization's overall growth strategy by aligning fundraising efforts with programmatic priorities and long-term financial sustainability. This role offers the opportunity to strengthen and scale a sophisticated development function, deepen engagement with Chicago's philanthropic and corporate communities, and expand the organization's pipeline of transformational giving.
The CDO will partner closely with the CEO and Board of Directors while leading a high-performing Development and Events team. This leader will also serve as a visible ambassador for After School Matters, building relationships that elevate the organization's profile and impact across the city and beyond.
Key Responsibilities:
Strategic Leadership & Fundraising
- Develop and execute a comprehensive, multi-year fundraising strategy to meet and exceed annual revenue goals
- Lead all aspects of philanthropic revenue, including individual giving, major and principal gifts, institutional giving, corporate partnerships, and planned giving
- Identify and pursue new funding opportunities that support organizational growth and innovation
- Provide strategic guidance on campaign planning and execution, including future capital or comprehensive campaigns
- Identify, prospect, and pursue government grant opportunities (local, state, and federal), in close collaboration with program, finance, and research teams to ensure alignment with organizational priorities and compliance requirements
Donor, Board & External Engagement
- Personally manage a portfolio of high-capacity donors and prospects, leading cultivation, solicitation, and stewardship efforts
- Partner with the CEO and Board of Directors to expand their engagement in fundraising and relationship-building
- Serve as a key external representative of the organization within Chicago's philanthropic, corporate, and civic communities
- Design and execute high-impact donor engagement strategies that strengthen retention, increase giving, and expand the prospect pipeline
Events, Campaigns & Donor Experience Strategy
- Provide strategic vision and leadership for After School Matters' portfolio of fundraising events, positioning them as key drivers of revenue, donor engagement, and brand visibility
- Lead the continued growth and evolution of the organization's signature events, including the Annual Gala and the Sneaker Ball, ensuring they deepen donor relationships, expand audience reach, and maximize net revenue
- Partner with the CEO, Board, and corporate stakeholders to leverage events as platforms for major gift cultivation, sponsorship growth, and community engagement
- Drive innovation in event strategy by exploring new formats, audiences, and partnerships that enhance long-term sustainability and visibility
- Establish clear performance metrics for events, aligning them with broader development goals such as donor acquisition, retention, and pipeline development
- Integrate event strategy into year-round fundraising efforts to create a cohesive and compelling donor journey
- Develop a plan to increase volunteer opportunities
Team Leadership & Development Operations
- Lead, coach, and develop a high-performing Development and Events team of 12, including direct reports
- Strengthen organizational capacity through talent development, performance management, and clear accountability structures
- Oversee development operations, including budgeting, forecasting, reporting, and systems (e.g., CRM platforms)
- Ensure strong alignment between Development, Finance, and Program teams to support organizational priorities
Experience & Qualifications:
- Bachelor's degree required; advanced degree preferred
- 10-15 years of progressive fundraising experience, including demonstrated success securing major and principal gifts (6 and 7 figures)
- Considerable experience leading development strategy within complex or high-growth organizations
- Proven ability to work effectively with boards and senior leadership in advancing fundraising outcomes
- Experience managing and developing teams, with a strong track record of building high-performing functions
- Knowledge of planned giving and/or experience with endowment campaigns
- Familiarity with Chicago philanthropic landscape preferred
- CRM use required, Raiser's Edge experience preferred
Leadership Competencies:
- Strategic and forward-thinking, with the ability to translate vision into actionable plans
- Results-driven, with a demonstrated ability to meet ambitious fundraising goals
- Strong relationship builder, with presence and credibility among senior stakeholders and donors
- Effective team leader who can inspire, develop, and retain talent
- Adaptable and entrepreneurial, with a willingness to lead through change and growth
Additional Information:
This role requires active participation in in-person meetings, donor engagements, and events, including evening and weekend commitments. Ability to travel to ASM sites as needed.
Benefits include:
- Medical, Dental, and Vision
- Medical and Dependent Care Flexible Spending Accounts
- Paid Parental Leave (PPL)
- Identity Theft, Legal, and Pet Insurance
- Paid Time Off (PTO), Paid Sick Time, and paid national holidays
Compensation: $176,000 - $195,000
