Associate Director of Major Gifts

Associate Director of Major Gifts

Reports to: Chief Development Officer

Salary Range: $90,000-$95,000

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.

The Associate Director develops and executes thoughtful strategies to secure significant annual, campaign, special project, and planned gifts while building meaningful, long-term donor relationships rooted in a shared passion for theater, education, and community impact. This role works closely with the Chief Development Officer, senior leadership, and colleagues across departments to deepen donor engagement and position CST for future growth.

The ideal candidate is an experienced and strategic relationship-builder with a strong track record of securing major gifts, managing complex donor relationships, and conveying the excitement and mission of a world-class arts 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

Core Competencies

• Exceptional relationship-building and interpersonal skills
• Strong emotional intelligence and donor-centered approach
• Strategic thinker with the ability to execute and close gifts successfully
• Persuasive communicator and compelling ambassador for CST’s mission
• Highly organized with strong project and portfolio management skills
• Self-directed, proactive, and accountable for fundraising performance
• Analytical and comfortable working with data, metrics, and reporting
• Collaborative, flexible, and solutions-oriented
• Passion for the performing arts and arts education

Qualifications

Required

• Bachelor’s degree or equivalent professional experience
• Minimum of five to seven years of frontline fundraising experience with a focus on major gifts
• Demonstrated success securing five- and six-figure gifts
• Experience managing donor portfolios and moves management strategy
• Experience working with a relational CRM database (Tessitura preferred)
• Ability to independently manage reporting, donor tracking, and portfolio analysis
• Strong written and verbal communication skills

Preferred

• Experience incorporating planned giving into donor strategies
• Experience in a performing arts, theater, or cultural organization
• Experience partnering with Board members and volunteer leadership on fundraising initiatives

Work Environment

• Standard hours: Monday–Friday, 9:00 am–5:00 pm
• Some evening and weekend work required for performances and events
• Primary worksite: Chicago Shakespeare Theater, Navy Pier

Physical Requirements

• Prolonged periods of sitting, standing, and computer work
• Ability to lift up to 10 pounds

Commitment to Equity, Diversity & Inclusion

CST is dedicated to increasing equity, diversity and inclusion in our audiences, our programs and in all our hiring for staff and artists. We are committed to providing a work environment that is free from discrimination. CST prohibits discrimination in employment against any employee or job applicant because of that person’s race, color, creed, religion, ancestry, sex, national origin, disability, genetic information, age, sexual orientation, gender identity, gender expression, marital status, familial status, veteran status, status with regard to public assistance, membership in a local human rights commission or any other legally protected status.