Deputy Director

Deputy Director
The Deputy Director serves as a strategic partner to the Executive Director and is charged with overseeing the programmatic operations of the organization, including the administration of the artist residency program, educational outreach, and public programs. This position combines high level strategic oversight with hands on staff management, ensuring effective mission delivery and meeting larger organizational goals and priorities. The successful candidate must be a highly collaborative leader who thrives on building systems, supporting artists, and helping to advance Ragdale’s mission through program development and external relationship building. This position is full-time, in-person and reporting to the Executive Director.

Qualifications

• Graduate degree in a relevant field or equivalent professional experience
• Experience working with artist residency programs
• A minimum of 7 years management experience in nonprofit or arts organizations with a proven track record of managing staff, interns and volunteers
• Experience managing data, compiling reporting, and developing narratives to effectively communicate organizational impact and outcomes
• Familiarity with strategic planning and organizational development
• Strong financial management skills developing, overseeing and managing budgets
• Excellent written and verbal communication skills for diverse audiences
• Experience working with databases, CRM software combined with a high level of competency developing spreadsheets and working within the Microsoft ecosystem
• Demonstrated ability to build collaborative relationships with staff, program participants, community partners, and board members
• Comfort with public speaking and making presentations
• Knowledge and understanding of the Chicago art and culture sector

Responsibilities

• Serve as strategic partner and support to the Executive Director to ensure the organization's programs, and policies are aligned to meet the goals and mission of the organization
• Direct the programmatic components of the organization including the artists in residence program and educational outreach to ensure programs center equity through organizational-wide practices, policies, and culture
• Oversee the design and implementation of the annual application cycle and direct policies and procedures for Ragdale programs including handbooks, and end of session evaluations
• Design the annual program schedule and oversee outreach and recruitment efforts for programs to align with organizational mission and goals. Serve as lead staff liaison to the Ragdale Curatorial Council by working closely with the chair of the council to oversee the artist in residence adjudication process;
• Cultivate, track, and sustain relationships with external organizational partners
• Serve as a member of the organization's senior leadership team aside the Director of Development and the Finance Director. Partner with the leadership team to develop program budgets, provide feedback on grants and relevant data for reporting, develop and manage program budgets
• Prepare program reports to present to the Board of Directors and participate in Board and related committee meetings
• Lead communications content generation related to programming to increase awareness and outreach and serve as a point of contact for programming with external communications firm
• Generate and maintain contracts for campus and facility rentals, creative sabbaticals, and themed residencies
• Mange and review staff, including the Residency program Manager, Program Facilities Coordinator, Housekeeping, and the Chef
• Attend board meetings prepare meeting reports as requested by the Executive Director
• Conduct and lead staff meeting in the absence of the Executive Director
• Participate in leadership meetings with external grant writers and participate in institutional advancement and identifying prospective funders
• Work with leadership team on planning and execution of special events
• Stay current on activity of current residents, fellows, and alumni

Compensation
The salary range for this position is $85,00-$100,000, commensurate with experience. This position also provides health and dental insurance, generous paid vacation time and participation in Ragdale’s 401(k) retirement plan.

About Ragdale
Ragdale is an artist residency program located in Lake Forest, Illinois, that provides time and space for artists to develop new works. Individuals apply through a competitive review process, and we award over 150 residencies annually, making Ragdale one of the largest residency programs in the United States. Ragdale also provides ways for people from broad backgrounds to participate in themed residencies, creative sabbaticals, outreach programs for teens, and public programs that connect Ragdale with the broader community. Situated on the grounds of the former summer home of noted Chicago architect Howard Van Doren Shaw and poet/playwright Frances Wells Shaw, Ragdale is a stunning example of Arts and Crafts Architecture and listed on the National Register. Comprised of a series of historic homes, purpose-built studios, and access to 50 acres of protected prairie land, Ragdale provides artists with a remarkable environment to explore their work. As an organization we believe that engagement with creativity is essential to a healthy and vibrant world, and our mission is to steward an inspirational environment that fosters courageous creativity and inclusive community through our artist residencies. www.ragdale.org

How to apply
For priority consideration, applications must be received by Friday, October 10, 2025. For consideration, please send a PDF cover letter detailing interest and relevant experience and complete resume to Paul Sacaridiz, Executive Director at jobs@ragdale.org, Subject Line: Deputy Director. If the candidate’s letter and resume reflect a fit for the position, they will be contacted for an interview. This position seeks to be filled no later than January 1, 2026. No phone calls, please.

Ragdale is committed to a culture of diversity, equity, and inclusion. As an organization we are dedicated to the fair and equal treatment of all our employees without regard to age, gender identification, race, color, religion, creed, national origin, ancestry, sexual orientation, disability, political affiliation, maternity status, parental status, military status, or any other basis prohibited by law. All are welcome.
Released September 8, 2025