Senior Director, Major Gifts

The Community Solution Education System; Chicago (IL); On-site; USD 140,000 - 190,000; Full time

Benefits offered by this job

Paid time‑off

Medical and dental coverage

Life and disability insurance

Retirement plan with employer match

Flexible spending accounts (FSA)

Tuition reimbursement

Professional development

Employee appreciation events

Job summary

The Chicago School is seeking a Senior Director, Major Gifts in Chicago to lead fundraising for four priority funds. You will build and own a major gifts book, cultivate six- and seven-figure gifts, and collaborate with the President and Executive Cabinet to position the institution for strategic opportunities.

This externally focused role requires ongoing donor engagement, proposal development, and stewardship to achieve annual fundraising goals, with travel as needed and a one-year employment

Qualifications

• 7+ years of frontline major gift fundraising experience
• Experience managing a personal portfolio of 50-75 major and principal gift prospects
• Some direct or matrixed management experience
• Familiarity with Chicago area funders, corporations, or foundations
• Experience building a fundraising pipeline and closing major gifts from limited infrastructure

Responsibilities

• Build and manage a portfolio of principal and major gift prospects from the ground up, personally driving each prospect through identification, qualification, cultivation, solicitation, and stewardship
• Prepare and negotiate proposals and gift agreements for six- and seven-figure commitments
• Build new relationships with local, regional, and national funders aligned to the four priority funds; conduct prospect research and identification as needed
• Design and execute donor stewardship plans for major donors, including gift acknowledgment, impact reporting, and ongoing engagement to ensure retention and upgrade of major and principal gift support
• Work with the President and Executive Cabinet to determine how best to position the institution for the four priority funding opportunities
• Manage and coach Major Gifts personnel; set portfolio strategy together and review pipeline moves regularly
• Oversee execution of employee and trustee giving campaigns, managed by Director, Major Gifts, ensuring alignment with overall fundraising strategy
• Coordinate with External Affairs teams and other institutional leaders to ensure a cohesive strategy in support of university goals
• Set annual fundraising goals in conjunction with the President
• Maintain and oversee accurate, timely records of all activity in Raiser’s Edge
• Report monthly on key metrics, including visits, proposals, and dollars raised against goal

Skills

Major gifts fundraising

Portfolio management

Donor cultivation & solicitation

Pipeline development

Leadership & collaboration

Education

Bachelor’s degree or equivalent experience

Tools

Raiser’s Edge

Job description

Job Description:

Position Summary

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 is a builder’s role with responsibility for establishing and growing a major gift prospect pipeline where limited fundraising infrastructure currently exists. You will identify, cultivate, solicit, and close six- and seven-figure gifts from individuals, corporations, and foundations, with fundraising focused on three core opportunities: The Chicago School Fund, the IllinoisCOM Fund, and the Clinical Psychology Impact Fellowship. You will work with the President and Executive Cabinet to determine how best to position the institution for these opportunities and build a donor pipeline where a limited one exists today.

This is an individual contributor fundraising position, not part of a large Advancement department. This role is best suited for a fundraiser who wants full ownership of a book of business with demonstrated ability to independently manage a major gift portfolio and achieve fundraising goals that advance the university’s mission.

The role is externally focused and based in Chicago, with an expectation that significant time will be spent engaging with donors and prospects outside the campus. Internal campaign management, including employee and trustee giving, is managed by the Director, Major Gifts. Occasional travel may be required.

The position is offered under an initial one-year employment agreement, with future renewal terms determined based on demonstrated performance and institutional needs.

What Success Looks Like

• A qualified pipeline of principal and major gift prospects, sufficient to support an annual goal of $1M in new commitments across the university’s priority funds

• Six- and seven-figure gifts and multi-year commitments secured against the Chicago School’s four priorities: The Chicago School Fund, the IllinoisCOM Fund, the Clinical Psychology Impact Fellowship, and NRCI

• A proposal-to-close ratio that reflects disciplined pipeline management, with prospects advancing consistently through identification, cultivation, solicitation, and stewardship

• Clear, accurate, and consistent reporting on critical KPIs that advance annual goals

Key Responsibilities

Portfolio Management & Closing Gifts

• Build and manage a portfolio of principal and major gift prospects from the ground up, personally driving each prospect through identification, qualification, cultivation, solicitation, and stewardship

• Prepare and negotiate proposals and gift agreements for six- and seven-figure commitments

• Build new relationships with local, regional, and national funders aligned to the four priority funds; conduct prospect research and identification as needed

• Design and execute donor stewardship plans for major donors, including gift acknowledgment, impact reporting, and ongoing engagement to ensure retention and upgrade of major and principal gift support

• Work with the President and Executive Cabinet to determine how best to position the institution for the four priority funding opportunities

Collaboration and Management

• Manage and coach Major Gifts personnel; set portfolio strategy together and review pipeline moves regularly

• Oversee execution of employee and trustee giving campaigns, managed by Director, Major Gifts, ensuring alignment with overall fundraising strategy

• Coordinate with External Affairs teams (including University Communications, Office of Sponsored Programs, Alumni Relations, and Public Affairs) and other institutional leaders as needed to ensure a cohesive strategy in support of university goals

Data Management and Reporting

• Set annual fundraising goals. in conjunction with the President

• Maintain and oversee accurate, timely records of all 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; support additional executive or board-level reporting as needed

Basic Qualifications

• Bachelor’s degree or equivalent experience

• 7+ years of frontline major gift fundraising experience, with a demonstrated track record of successfully 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 from limited infrastructure

Preferred Qualifications

• 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 preferred)

The Chicago School offers a generous compensation and benefits package, as well as the opportunity to work for a leader in the field of education. Some of our key benefits include: generous paid time-off, medical and dental coverage, company-paid life and disability insurance, retirement plan with employer contribution, multiple flexible spending accounts (FSA), tuition reimbursement, professional development, and regular employee appreciation events.

The Chicago School is an Equal Opportunity Employer.

Company:

The Chicago School