Associate Director of Major Gifts

Position Summary

The Associate Director of Major Gifts is a frontline fundraising professional responsible for the cultivation, solicitation, stewardship, and long-term engagement of Chicago Shakespeare Theater’s major donors and prospects. This position manages a dynamic portfolio of individuals capable of making gifts of $10,000 and above and plays a critical role in advancing CST’s contributed revenue goals and strengthening a culture of philanthropy across the organization.

Major Gift Fundraising & Donor Management

• Manage and grow a robust portfolio of major donors and high-capacity prospects with clearly defined revenue and engagement goals
• Develop and execute individualized cultivation, solicitation, stewardship, and upgrade strategies for assigned donors and prospects
• Conduct regular in-person donor meetings, outreach, and solicitations to deepen relationships and secure philanthropic support
• Secure major gifts in support of annual operations, artistic programming, education initiatives, special projects, and future campaign priorities
• Build and maintain a strong pipeline of prospective donors through strategic identification, qualification, and relationship development
• Partner with the Chief Development Officer on top-tier donor strategy, leadership giving opportunities, and select solicitations
• Prepare donor briefings, proposals, talking points, and strategic materials for leadership and volunteer engagement
• Support and partner with Board members and senior volunteers in cultivation and solicitation activities where appropriate
• Meet or exceed annual fundraising and portfolio performance goals and key performance indicators
• Create meaningful and memorable donor experiences, including behind-the-scenes opportunities, artist interactions, rehearsals, performances, and special events

Planned Giving & Long-Term Donor Strategy

• Integrate planned giving into donor conversations as part of long-term relationship management and stewardship
• Partner with leadership to strengthen and grow CST’s planned giving prospects within the major gifts portfolio
• Track and manage planned giving prospects, intentions, and commitments in Tessitura
• Develop planned giving messaging, donor engagement strategies, and marketing materials across print and digital platforms
• Help position the organization for future endowment and campaign growth through strategic donor development

Data Management, Reporting & Portfolio Strategy

• Maintain accurate, timely, and detailed donor records, contact reports, and moves-management activity in Tessitura
• Independently manage portfolio tracking, reporting, forecasting, and next-step strategy for all assigned prospects
• Develop donor profiles, research summaries, segmentation strategies, and briefing materials to support cultivation and solicitation efforts
• Analyze portfolio performance and donor trends to inform strategy and maximize fundraising success
• Ensure donor interactions and engagement activity are documented consistently and strategically
• Participate in contributed revenue forecasting, pipeline review, and fundraising planning efforts

Collaboration & Institutional Engagement

• Partner with Development colleagues to support fundraising initiatives, donor events, and the annual Gala
• Collaborate with the Associate Director of Individual Giving to transition and elevate qualified donors into the major gift pipeline
• Work collaboratively with Institutional Giving and senior leadership to align fundraising strategies and donor engagement opportunities
• Collaborate with colleagues across Marketing, Communications, Education & Lifelong Learning, and Artistic departments to strengthen donor storytelling and engagement
• Represent Chicago Shakespeare Theater with professionalism, enthusiasm, and a strong commitment to the organization’s mission and values in all interactions