Director of Major Gifts

Greenwood Project

Director of Major Gifts driving relationships for fundraising at Greenwood Project. Seeking candidates with experience in high-level sales or major gifts fundraising to join during growth phase.

Posted 4/22/2026full-timeChicago • Illinois • 🇺🇸 United StatesLead💰 $110,000 - $125,000 per yearWebsite

About the role

Key responsibilities & impact

Own and execute a revenue growth strategy that secures $1M+ annually from individuals, foundations, and corporate partners, with an emphasis on closing five- and six-figure deals.
Build and execute a cultivation strategy targeting new high-net-worth individuals, family foundations, and institutional funders. Maintain pipeline of 75+ qualified prospects with systematic relationship building and strategic follow-up.
Own end-to-end major gift process from prospect research to cultivation, proposal development, solicitation meetings, and stewardship - driving five and six-figure commitments.
Collaborate with the CEO and cross-functional teams (Programs, Partnerships, Governing Board, Young Professionals Board) to align donor engagement with organizational priorities.
Implement and manage the infrastructure that drives success; CRM tracking, reporting, pipeline forecasting, and performance metrics. Maintain pipeline discipline with systematic relationship tracking across all prospect interactions.
Represent Greenwood Project at high-level meetings and events, delivering compelling pitches that clearly communicate ROI and impact for partners and donors.

Requirements

What you’ll need

5–7+ years of experience in high-level sales, business development, or account management with a track record of closing significant accounts or partnerships. OR equivalent experience in major gifts fundraising with a strong record of securing five- and six-figure gifts. We’re especially interested in sales professionals eager to apply their skills in a mission-driven setting
Excellent relationship management and communication skills
Self-starter with exceptional organizational discipline and strategic thinking - a prospecting athlete comfortable managing complex, long-cycle relationships
Proficiency in CRM platforms (HubSpot preferred)
Deep commitment to Greenwood’s mission of education, access, and workforce development
Familiarity with Chicago’s philanthropic community is helpful, but we are equally enthusiastic about candidates from sales or business development backgrounds who are excited to apply their expertise in a new and impactful space
Experience driving revenue through sales, account management, business development, or fundraising, in the education, workforce development, finance, or other growth-oriented sectors
Knowledge of corporate sponsorships, foundation grants, and donor events is valuable
Familiarity with the financial services industry is also a strong plus

Benefits

Comp & perks

access to employee health care
dental and vision coverage
disability insurance
401(k) plan
generous paid time off

ATS Keywords

✓ Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

revenue growth strategymajor gift processprospect researchcultivation strategyproposal developmentsolicitation meetingsCRM trackingpipeline forecastingperformance metricsrelationship tracking

Soft Skills

relationship managementcommunication skillsorganizational disciplinestrategic thinkingself-starterprospectingcollaborationpresentation skillssystematic follow-uppipeline discipline