Weekend Shakespeare Theater Jobs (NOW HIRING)

Associate Director of Individual Giving

Reports to: Chief Development Officer

Salary Range: $82,000-$86,000

Position Summary

The Associate Director of Individual Giving is responsible for the identification, cultivation, solicitation, and stewardship of Chicago Shakespeare Theater’s individual donors, with a focus on gifts from $1,000 to $9,999 (Bard Circle). This role leads and implements the strategy for annual giving and plays a key role in building a strong pipeline of future major donors.

This is a frontline fundraising role that manages a dynamic portfolio of donors and prospects, drives annual fund growth, and ensures consistent donor engagement, retention, and movement through the giving pipeline. The Associate Director is expected to bring both strategic thinking and hands-on execution to all aspects of individual giving.

Individual Giving & Donor Management

• Manage a portfolio of approximately 150–200 donors and prospects within the $1,000–$9,999 range
• Develop and implement individualized cultivation, solicitation, and stewardship strategies tailored to each donor
• Conduct regular donor outreach, including in-person meetings, calls, and written communications
• Engage donors at performances, events and across Theater programs to deepen connection and affinity
• Solicit annual gifts and upgrades to increase donor retention and overall revenue
• Maintain consistent, thoughtful engagement with donors to strengthen long-term relationships and increase lifetime value

Annual Fund Strategy & Execution

• Lead and implement strategy for the Theater’s annual fund, including segmentation, messaging, and upgrade pathways
• Develop robust and innovative targeted strategies for donor acquisition, retention, and re-engagement, including LYBUNT and SYBUNT initiatives
• Partner with the Development Operations team to execute appeals and campaigns while maintaining ownership of strategy and outcomes
• Analyze campaign performance and adjust strategies to maximize participation, retention and revenue growth
• Write, develop, and manage compelling annual giving solicitation mailings and campaigns in collaboration with the CDO, Associate Director of Major Gifts, Development Operations Manager, and Marketing

Pipeline Development & Donor Growth

• Identify and qualify donors with capacity and inclination for major giving
• Partner with the Associate Director of Major Gifts to transition donors into higher-level portfolios
• Track donor movement and progression across giving levels to ensure a strong and active pipeline
• Proactively identify opportunities to deepen engagement and increase giving across the portfolio

Data Management, Reporting & Strategy

• Maintain accurate, timely, and detailed donor records, contact reports, and moves management activity in Tessitura
• Independently manage portfolio reporting, segmentation, and performance tracking
• Develop donor profiles, briefing materials, and targeted segmentation strategies to support cultivation and solicitation
• Analyze donor behavior, campaign results, and giving trends to inform strategy and decision-making
• Ensure all donor interactions are consistently documented and aligned with overall fundraising strategy and goals

Donor Engagement & Events

• Support and participate in donor events, including cultivation and stewardship activities
• Partner with Development colleagues to ensure strong follow-up and meaningful engagement after events and campaigns
• Develop, organize, host 2-3 Bard Circle events and 1-2 annual giving events per fiscal year.

Core Competencies

• Strong relationship-building and communication skills
• Strategic thinking with strong attention to detail
• Ability to manage multiple priorities and deadlines in a fast-paced environment
• Analytical and comfortable working with donor data, segmentation, and reporting
• Strong persuasive and donor-centered writing skills
• Self-directed, proactive, and accountable for results
• Professional, collaborative, and solutions-oriented
• Passion for theater and the performing arts

Qualifications

Required

• Bachelor’s degree or equivalent experience
• Minimum of five years of experience in fundraising, with a focus on individual giving or annual fund
• Proven ability to manage a donor portfolio and meet or exceed revenue goals
• Experience working with a relational CRM (Tessitura preferred)
• Ability to independently manage reporting, segmentation, and donor tracking

Preferred

• Experience in a performing arts or cultural organization

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.