Executive Director: Lead Community Journalism (Flexible Schedule)

South Side Weekly; Chicago (IL); Hybrid; USD 75,000 - 80,000; Full time

Benefits offered by this job

Health insurance reimbursement

Flexible work schedule

30 PTO days

Health days

Job summary

South Side Media Works is seeking an Executive Director to oversee the publishing operations for South Side Weekly and Hyde Park Herald. The ED will lead budgeting, fundraising, audience growth, and strategic planning in collaboration with the Board of Directors.

The role requires strong nonprofit leadership, fundraising acumen, and proven ability to manage complex operations. In-person work at our Woodlawn office will be required, with opportunities for flexible scheduling.

Qualifications

• Deep commitment to local civic and cultural institutions.
• Experience defining and implementing strategy and leading a team.
• Fundraising experience with nonprofits or community projects.
• Hands-on budget management and financial controls.
• Strong communicator capable of motivating volunteers and staff.
• Interest and connections to the South Side of Chicago.

Responsibilities

• Lead all publishing operations for South Side Weekly and Hyde Park Herald.
• Develop and manage the annual budget and funding plan (subscriptions, ads, donations, grants).
• Design clear audience growth strategies in partnership with editorial leadership.
• Ensure administrative systems run smoothly and board/funders are engaged.
• Set measurable goals and support staff with clear accountability.
• Build and maintain partnerships with funders, donors, and community stakeholders.

Skills

Community journalism

Strategic leadership

Fundraising

Budget management

Communication

Team motivation

Humility & learning

South Side ties

Tools

Project management tools

Job description

South Side Media Works is seeking an Executive Director to oversee the publishing operations for South Side Weekly and Hyde Park Herald. The ED will lead budgeting, fundraising, audience growth, and strategic planning in collaboration with the Board of Directors.

The role requires strong nonprofit leadership, fundraising acumen, and proven ability to manage complex operations. In-person work at our Woodlawn office will be required, with opportunities for flexible scheduling.