Director of Development

Lookingglass Theatre Company; Chicago (IL); Hybrid; USD 77,000 - 94,000; Full time

Benefits offered by this job

Health Insurance

Vision & Rx plan

12 paid holidays

Vacation, Personal, Sick time-off

Job summary

Lookingglass Theatre Company seeks a collaborative, entrepreneurial Director of Development to build a sustainable contributed-revenue program and strengthen donor relationships. You will lead a small development team, coordinate across departments, and report to the Executive Director.

With 5-7 years of nonprofit fundraising experience, you will manage major gifts, institutional giving, and campaigns while guiding development operations and donor stewardship in a dynamic theatre environment.

Qualifications

• 5-7 years of nonprofit fundraising experience with increasing leadership responsibility.
• Ability to develop and execute fundraising strategies across major gifts, institutional, and campaigns.
• Strong writing, communication, and organizational skills; proficient with fundraising data and CRM.

Responsibilities

• Lead annual and multi-year contributed-revenue goals and fundraising plans.
• Manage a portfolio of donors, cultivate major gifts, and steward relationships with boards.
• Oversee foundation, corporate, government, and institutional funding; supervise Grants Manager.
• Provide development operations oversight, CRM records maintenance, and reporting.
• Collaborate with leadership and artistic teams to align fundraising with artistic priorities.

Skills

Donor relations

Leadership

Fundraising strategy

CRM systems

Storytelling

Budgeting

Tools

CRM systems

Job description

Director of Development

Reports to: Executive Director
Classification: Full-time, Exempt
Supervises: Donor Engagement Manager, Grants Manager (part-time), Development Operations Coordinator (part-time)
Salary: $85,000 annually
Work Location: Work from Lookingglass offices at 190 E Delaware Pl. Chicago, IL four days a week (Tuesday – Friday); work from home option for Mondays. Occasional evening and weekend events.

Application Deadline: December 1, 2026

About Lookingglass Theatre Company

Lookingglass Theatre Company is the largest ensemble-based theatre in America dedicated to the creation of new work. Guided by its core values of Invention, Collaboration, and Transformation, Lookingglass reimagines the possibilities of live performance with every production, seeking to make theatre more exhilarating, inspirational, and accessible to all.

Founded in 1988 by a group of Northwestern University theatre graduates, Lookingglass made its permanent home in 2003 in the historic Water Tower Water Works on Chicago’s Magnificent Mile. Since its founding, the Company has produced more than 75 world premieres and received the 2011 Regional Tony Award for Artistic Achievement.

With a roster of 33 Ensemble Members and 17 Artistic Associates, Lookingglass draws on a uniquely interdisciplinary approach to theatre‑making, bringing together artists trained in theatre, dance, design, music, and circus arts. At the heart of every production is the ensemble: a shared spirit of invention, a commitment to collaboration, and an appetite for transforming the theatrical experience.

Position Overview

Lookingglass seeks a collaborative, entrepreneurial Director of Development to help shape this next chapter, building the philanthropic relationships and resources that make daring artistic work possible.

The Director will lead a sustainable contributed‑revenue program, deepen relationships with donors and institutional partners, guide a small development team, and strengthen the systems needed to support Lookingglass’s artistic ambitions and long‑term stability.

Working closely with the Executive Director, Producing Director, Board, Artistic Directors, Ensemble, and colleagues across the company, the Director will balance strategic leadership with hands‑on execution. The Executive Director, Producing Director, Artistic Directors, Board Development Chair and Board Chair will be an active fundraising partners, particularly in key leadership donor and Board relationships. Portfolio ownership and coordinated solicitation plans will be developed together with the Director of Development.

This is an opportunity for a person who is eager to grow into this leadership role, who enjoys building relationships, bringing creative ideas to life, and creating the systems and structure needed in this dynamic, collaborative environment.

Key Responsibilities

Fundraising Strategy & Leadership

• Partner with the Executive Director to establish annual and multi‑year contributed‑revenue goals, fundraising plans, calendars, and performance measures that advance Lookingglass’s artistic and institutional priorities.
• Lead and coach the development team, establish priorities, coordinate workloads, and ensure effective execution and follow‑through.
• Oversee individual, institutional, corporate, government, event, and campaign fundraising, monitoring progress, risks, and opportunities.
• Foster a collaborative culture of philanthropy that engages staff, Board members, artists, and other advocates in supporting Lookingglass’s mission.

Individual Giving, Major Gifts & Board Engagement

• Lead annual giving, donor renewals, major‑gift prospect development, and stewardship strategy in partnership with the Donor Engagement Manager.
• Manage a portfolio of major donor prospects; partner with the Executive Director and volunteer leaders on cultivation, solicitation, and stewardship.
• Build meaningful connections between donors and Lookingglass’s artists, productions, creative process, and institutional vision.
• Equip Board members, Artistic Leadership, and Ensemble members with coordinated opportunities, briefings, and meaningful roles in donor engagement.
• Attend Board meetings and prepare development reports that communicate fundraising progress, priorities, opportunities, and challenges.
• Staff the Board’s Development Committee, including coordinating meetings, preparing materials, and supporting committee members in their fundraising roles.

Institutional, Corporate & Campaign Giving

• Provide strategic oversight of foundation, corporate, and government funding, including prospect priorities, grant calendars, proposals, reports, and stewardship; supervise the Grants Manager’s day‑to‑day work.
• Develop sponsorship and institutional partnership opportunities that connect funders with Lookingglass’s productions, artistic development, education programs, and community engagement.
• Coordinate fundraising plans and prospect management for multi‑year campaigns and major institutional initiatives, including Lookingglass’s home at the Water Tower Water Works.

Events & Donor Experiences

• Provide fundraising direction and oversight for Lookingglass’s signature Come As You Aren’t gala and a focused calendar of cultivation and stewardship events, with the Donor Engagement Manager leading event planning and execution.
• Collaborate with artists and colleagues to create distinctive donor experiences that reflect Lookingglass’s creativity, storytelling, and spirit of invention.
• Ensure events have clear revenue or relationship objectives, disciplined budgets, effective guest strategies, and timely follow‑up.

Development Operations & Cross‑Functional Partnership

• Oversee accurate CRM records, gift and pledge processing, donor acknowledgments, prospect tracking, and useful fundraising reporting, with day‑to‑day execution delegated appropriately to the Development Operations Coordinator and other team members.
• Partner with the General Manager on development budgets, restricted gifts, reconciliation, cash‑flow projections, fundraising forecasts, and event financial planning.
• Collaborate with artistic, programming, and marketing colleagues to communicate Lookingglass’s work and impact through compelling proposals, appeals, and donor communications.

Qualifications & Leadership Attributes

• 5-7 years of nonprofit fundraising experience with increasing leadership responsibility.
  Demonstrated ability to develop and execute fundraising strategies, aligning people, resources, and operational processes to achieve goals.
• Skill in cultivating donor relationships, coaching staff and volunteers, and managing multiple fundraising programs.
• Strong writing, communication, organizational, financial, and decision‑making skills; comfort using CRM systems and fundraising data.
• A collaborative, resourceful, and adaptable approach, with the ability to balance strategic thinking and hands‑on work.
• Curiosity about the creative process, enthusiasm for live theatre, and an appreciation for the role of artists and storytelling in bringing people together.
• Relevant transferable leadership experience is welcome; professional theatre experience and a particular degree are not required.

First‑Year Priorities

Working in close partnership with the Executive Director, the Director of Development will focus on building a strong foundation for Lookingglass’s next chapter. Priorities include establishing a clear development plan and major‑gift pipeline; strengthening donor renewal and stewardship; maintaining a coordinated institutional‑giving program; improving revenue forecasting and reporting; engaging Board members and artists in fundraising; and aligning staffing and operations to support sustainable contributed‑revenue growth.

Benefits

• Health Insurance (choice of PPO or HMO; Organization covers the cost of 100% of the HMO plan for the employee. If PPO plan is elected, staff members pays the difference between the PPO plan and the HMO plan. This is reevaluated annually in July with the adoption of the health plan).
• Vision & Rx plan;
• 12 paid holidays; and
• Vacation, Personal, Sick time‑off.

Lookingglass recognizes that candidates may not meet every qualification listed and welcomes applicants whose experience, skills, and interests align with the spirit of the role.

Lookingglass Theatre Company is an Equal Opportunity Employer committed to fostering a diverse, inclusive, and equitable workplace. We recruit, hire, develop, and retain employees without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, ancestry, age, disability, genetic information, marital status, veteran status, citizenship status, or any other characteristic protected by applicable federal, state, or local law. We welcome applicants from all backgrounds and experiences.

Lookingglass Theatre Company is committed to providing reasonable accommodations to qualified individuals with disabilities throughout the application and employment process. Applicants requiring accommodation to participate in the recruitment process are encouraged to contact the Company.