Associate Director of Individual Giving

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…