Strategic and Organizational Leadership

• Develop and execute a strategic vision and operating plan that honors Lillstreet’s core identity while guiding the organization’s long-term growth and sustainability.

• Translate the owner’s vision into clear, executable goals and objectives that align staff, programming, and resources.

• Build and maintain partnerships and alliances that expand Lillstreet’s audience, reach, and community relevance.

• Serve as an external ambassador for Lillstreet, representing the organization with community partners, civic institutions, and the broader arts arena.

• Facilitate with the owner the creation of an Advisory Board.

Financial and Operational Management

• Oversee the day-to-day operations of Lillstreet, ensuring efficiency, compliance, and alignment with organizational values.

• Develop and manage annual operating budgets, maintaining a longer-term financial perspective.

• Identify and pursue revenue strategies including programming and earned income options.

• Ensure financial reporting is accurate, transparent, and communicated effectively to the owner and soon-to-be-established Advisory Board.

Staff Leadership and Culture

• Foster a positive, transparent, and collaborative work environment that supports staff excellence, professional growth, and accountability.

• Work closely with the Human Resources Consultant to understand staffing dynamics, staffing roles and staffing needs.

• Hire, supervise, and develop the leadership team, with an eye toward building a strong institution from within.

• Establish clear lines of accountability while maintaining the open, community-centered culture Lillstreet is known for.

Community and Programming

• Maintain a deep understanding of and genuine appreciation for Lillstreet’s programming, including classes, open studio, artist studios, gallery, and community events.

• Engage directly with the Lillstreet community, including students, teachers, and resident artists, as a visible and approachable leader

• Commit to taking Lillstreet classes (upon hire) to build authentic relationships and a firsthand understanding of the Lillstreet experience.

• Establish relationships with a diverse range of Chicago-based art and maker studios to build a supportive community of practice.

Ideal candidates will bring a demonstrated record of leadership in an arts, culture, or creative organization and a genuine connection to Chicago’s creative community. They will combine strong management instincts with the relational intelligence to build trust across a staff and community that cares deeply about this place.

Desired Skills and Experience

• A minimum of ten years experience managing an arts, culture or similar organization, including staff, programming, and financial operations.

• Excellent written and verbal communication skills.

• Organizational administrative expertise, including budgeting, financial planning, and operational oversight.

• Comfort navigating organizational transitions, including building accountability structures while preserving institutional culture.

• Demonstrated ability to provide clear, collaborative, and transparent leadership across a diverse staff.

• A long-term orientation: ability to balance short-term organizational needs with a vision that guides ongoing leadership decisions.

• Experience developing, working with and reporting to an Advisory Board.

• Familiarity with Chicago’s arts, culture, and community landscape.

• Ability to navigate complicated dynamics in a gracious and responsive manner.

• Warm, personable, and approachable leadership style with strong emotional intelligence and active listening skills.

• Appreciation for and genuine interest in the breadth of mediums and depth of classes cultivated in Lillstreet’s creative community