Senior Director, Major Gifts

The Community Solution Education System•Chicago, IL

2d•Onsite

About The Position

The Senior Director, Major Gifts is the lead individual fundraiser driving philanthropic support for The Chicago School, including the Illinois College of Osteopathic Medicine. This builder role establishes and grows a major-gift prospect pipeline where limited fundraising infrastructure currently exists. The Senior Director identifies, cultivates, solicits, and closes six- and seven-figure gifts from individuals, corporations, and foundations, focusing on The Chicago School Fund, the IllinoisCOM Fund, the Clinical Psychology Impact Fellowship, and NRCI. This individual-contributor fundraising position offers ownership of a major-gift portfolio and requires independently managing prospects and achieving fundraising goals. The role is externally focused and based in Chicago, with significant time spent engaging donors and prospects away from campus. Occasional travel may be required. Internal campaign management, including employee and trustee giving, is managed by the Director, Major Gifts. The position is offered under an initial one-year employment agreement; future renewal terms depend on demonstrated performance and institutional needs. The successful candidate will build a qualified principal and major-gift pipeline sufficient to support an annual goal of $1 million in new commitments across university priority funds; secure six- and seven-figure gifts and multi-year commitments; advance prospects through identification, cultivation, solicitation, and stewardship; and provide clear, accurate reporting on key fundraising metrics.

Requirements

Bachelor's degree or equivalent experience.
At least 7 years of frontline major-gift fundraising experience, with a demonstrated track record of closing six- or seven-figure gifts.
Experience managing a personal portfolio of 50–75 major and principal-gift prospects.
Some direct or matrixed management experience, such as managing or coaching a coordinator or junior fundraiser.
Familiarity and experience with Chicago-area funders, corporations, or foundations.
Experience building a fundraising pipeline and closing major gifts with limited infrastructure.

Nice To Haves

Experience fundraising in higher education, healthcare, or academic medicine.
Experience partnering directly with a president, CEO, or executive leadership team on fundraising strategy and execution.
Familiarity with clinical psychology, mental health, or osteopathic medicine as a philanthropic priority area.
Proficiency with a donor CRM; Raiser's Edge is preferred.

Responsibilities

Build and manage a portfolio of principal and major-gift prospects, personally guiding each through identification, qualification, cultivation, solicitation, and stewardship.
Prepare and negotiate proposals and gift agreements for six- and seven-figure commitments.
Build relationships with local, regional, and national funders aligned with the priority funds, conducting prospect research and identification as needed.
Design and execute stewardship plans for major donors, including acknowledgments, impact reporting, and ongoing engagement to support retention and upgrades.
Work with the President and Executive Cabinet to position the institution for its priority funding opportunities.
Manage and coach Major Gifts personnel, set portfolio strategy together, and regularly review pipeline moves.
Oversee execution of employee and trustee giving campaigns managed by the Director, Major Gifts, ensuring alignment with overall fundraising strategy.
Coordinate with External Affairs teams, including University Communications, the Office of Sponsored Programs, Alumni Relations, and Public Affairs, and with other institutional leaders to support university goals.
Set annual fundraising goals in conjunction with the President.
Maintain and oversee accurate, timely records of activity, moves, and next steps in Raiser's Edge, ensuring team compliance with university policies and procedures.
Report monthly on key metrics, including visits, proposals, and dollars raised against goal, and support additional executive- or board-level reporting as needed.