Director of Major Gifts & Individual Giving

KIPP Chicago • Chicago, IL

2d • Onsite

About The Position

KIPP Chicago’s Director of Major Gifts & Individual Giving is a new, key role for our organization. The Director of Major Gifts & Individual Giving will generate and manage a portfolio of high-capacity donors and prospects, deepen engagement, and secure leadership and major gifts that advance KIPP Chicago’s long-term vision for students and families. In this role, the Director of Major Gifts & Individual Giving will expand and lead our individual giving program in support of our $25M 25th Anniversary “Path to Freedom” Campaign. The position is located in Chicago and requires daily, consistent presence in Chicago, with the expectation of being actively in the field for outreach and relationship meetings, both during the day, in the evening, and on weekends when necessary – and with some time being spent in our regional office in Pilsen.

Requirements

• 5–7+ years of progressive fundraising experience, with a focus on individual and major gifts.
• Ability to work in-person, daily in Chicago in both our Pilsen office and in the field for necessary donor cultivation, and flexibly for weekend and evening events when required
• Demonstrated success securing at least low- to mid-five-figure gifts; experience closing six-figure gifts and multi-year commitments strongly preferred.
• Proven ability to manage a major gift portfolio, including prospect research, moves management, and revenue forecasting.
• Excellent interpersonal, communication, and presentation skills, with the ability to build trust and inspire confidence with high-net-worth individuals.
• Strategic thinker with strong planning, organizational, and follow-through skills; comfortable working both independently and as part of a collaborative team.
• High degree of professionalism, discretion, and sound judgment.
• Commitment to educational equity and to KIPP Chicago’s mission; familiarity with the Chicago philanthropic community is a plus.

Responsibilities

• Strategic Leadership of Individual Giving and Campaign
• Design and implement an individual giving strategy aligned with KIPP Chicago’s $25M 25th Anniversary Campaign goals, including annual, multi-year, and transformational gifts.
• Develop short- and long-term revenue projections and donor pipelines in collaboration with the Chief External Affairs Officer and campaign leadership.
• Support the creation and refinement of the campaign case for support, gift tables, naming opportunities, and donor recognition plans.
• Portfolio Management and Donor Fundraising
• Manage a portfolio of approximately 100–150 major gift prospects, ensuring regular and meaningful contact, movement through the donor cycle, and robust revenue outcomes.
• Conduct ongoing prospect identification, qualification, and prioritization to build and refresh the major gifts pipeline.
• Create and execute individualized cultivation and solicitation strategies, including setting clear financial goals and timelines for each prospect.
• Personally solicit 5- to 7-figure gifts and multi-year pledges; prepare leadership and volunteers for high-level solicitations as appropriate.
• Ensure high-quality stewardship through personalized follow-up, impact reporting, recognition, and ongoing engagement opportunities.
• Collaboration with Leadership, Board, and Staff
• Work closely with the CEO, Chief External Affairs Officer, board members, and campaign volunteers to plan and execute prospect strategies and solicitations.
• Provide coaching, briefing materials, and talking points for leaders and volunteers participating in donor meetings and events.
• Collaborate with the broader development and communications team to align major gifts with annual giving, events, corporate/foundation relations, and marketing.
• Systems, Data, and Reporting
• Maintain accurate and timely records of donor interactions, moves management, proposals, and revenue in the organization’s CRM.
• Track and report on individual giving metrics, including portfolio activity, pipeline growth, and campaign progress.
• Use data to inform decisions about portfolio composition, donor strategies, and resource allocation.
• Events and Donor Engagement
• Conceptualize and support small, high-impact cultivation and stewardship events and experiences tied to the anniversary campaign.
• Partner with program and school-based staff to design site visits and other mission-immersive experiences for donors and prospects.

Benefits

• Competitive executive salary, commensurate with experience and aligned to regional salary bands
• Competitive rates for medical insurance and short-term disability insurance.
• Dental insurance, vision insurance, life insurance, and long-term disability insurance are offered at no cost.
• Competitive retirement savings benefits: Chicago Teachers Pension Fund eligibility for IL licensed educators or 403B match
• Robust development and professional collaboration within national KIPP Foundation CSO cohort

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 501-1,000 employees