Deputy Director

Website FreeSpiritChi Free Spirit Media

Media education organization

Free Spirit Media

Job Title: Deputy Director

Reports To: Executive Director

Supervises: Program Managers



The Deputy Director will partner with the Executive Director to oversee communications, development, operations, and especially programmatic functions for Free Spirit Media. The Deputy Director will play a vital role in connecting key strategic and programmatic priorities to initiatives and frameworks for their activation and integration. The Deputy Director position is new to Free Spirit Media; the vision for this position is to help connect organization vision, values, and implementation efforts. The Deputy Director will be a key leader in the organization, interfacing both with internal team members and stakeholders and with external partners, allies, and prospective supporters.

Essential Duties and Responsibilities


Management & Executive Efforts (35%)

·         Oversee strategic plan implementation and ensure organization is tracking to and meeting goals

·         Interface with board, board committees, staff, staff committees, youth council, and stakeholders to advance strategic priorities

·         Oversee, develop, and streamline database and contact management systems

·         Co-plan and co-facilitate meetings

·         Oversee staff work plans, deliverables, and outcome schedules

·         Ensure partner check-ins are scheduled and deliverables are met

·         Represent organization at various functions

·         Other duties as assigned


Programmatic Efforts (30%)

·         Oversee Program Managers to ensure successful programming in the areas of in-school, out-of-school, and pathways programming

·         Ensure and evaluate how youth development and media production best-practices are being modeled and promoted across all program offerings

·         Oversee organization’s evaluation, assessment, and outcome tracking efforts; ensure outcomes are being met linked to the organization’s logic model

·         Ensure proper recordkeeping and program reporting

·         Support program team in grant writing and reporting components

·         Support successful youth and young adult-focused events including banquets, showcases, and workshops

·         Support Program Managers and staff in advancing organizational goals and culture

·         Other duties as assigned



Development Efforts (20%)

·         Interface with Development team on institutional fundraising strategies

·         Support Development team to ensure successful partnerships with supporters

·         Represent organization in outreach and stewardship functions

·         Network to expand donor and partner base

·         Support the organization’s special event initiatives

·         Work with high-level organization volunteers to advance development efforts

·         Support key donor strategies

·         Other duties as assigned


Communications & Distribution Efforts (15%)

·         Support Communications team to ensure successful communications efforts through social media, newsletter, website, and other communications vehicles

·         Support Communications team on growing organization’s brand externally

·         Promote youth-made media to current and prospective external distribution partners

·         Promote staff and organization via conferences, panels, and media opportunities

·         Other duties as assigned

Qualifications, Education and/or Experience

·         Bachelor’s degree or greater from a four-year college or university preferred

·         7+ years experience in non-profit management, programming, fundraising, and communications

·         Experience with media arts, youth development, and/or social justice organizations preferred

·         Experience leading, developing, and supervising a strong team

·         Experience in program design and facilitation

·         Expertise in evaluation design and implementation

·         Excellent managerial skills, experience working cross-departmentally, and proven track record of building systems and processes for organizational sustainability

·         Solid knowledge of foundation, corporate, individual, and government giving

·         Knowledge of the local and national funding community with a focus on media arts funders and individual philanthropists preferred

·         Knowledge of non-profit human resources, finance, and operations


Work Requirements:

This is a full-time position.  Hours may exceed 40 hours per/week.  Free Spirit Media is an equal opportunity employer.  Ability to drive and/or own a reliable vehicle is strongly recommended.


Compensation & Benefits:

Salary: Competitive and commensurate with education and experience; Range $65,000 – $72,000

Benefits: Competitive package including healthcare, dental, and vision; IRA match after 1 year

Paid Time Off: 18 Paid Time Off days accrued during first year in addition to 16 paid holidays

Professional development: Funds available to support staff in achieving career objectives


To Apply:

Please e-mail resume, cover letter and salary history to with subject line: Deputy Director: {Your Name}.


Free Spirit Media is an equal opportunity employer committed to fostering a diverse and equitable environment in which all staff can excel regardless of race, ethnicity, age, faith, gender identity, sexual orientation, and ability. People of color, women, individuals with disabilities and veterans are encouraged to apply.


About Free Spirit Media:

The mission of Free Spirit Media is to cultivate diverse youth voices to transform media and society. Free Spirit Media provides youth on Chicago’s South and West sides with a comprehensive foundation in media literacy and a hands-on media production experience through a youth development lens. We employ a holistic program model to develop youth into productive, connected, and engaged adults. Since our founding in 2001, Free Spirit Media has empowered more than 5,500 youth to share their stories, discover their potential, and engage their peers and communities through digital media. Free Spirit Media’s programming includes school-based media arts education, after school digital media programs, and advanced pathways programs that connect participants with opportunities in professional media industries. Participants at all ages and levels of our programming are supported in developing 21st Century skills that prepare them for success in college and careers. Please see for more information.

To apply for this job email your details to