Executive Director

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

Job summary

South Side Media Works in Chicago is seeking an Executive Director to lead publishing operations for the South Side Weekly and Hyde Park Herald. The ED will shape annual budgeting, fundraising strategy, and board relations to sustain local journalism on the South Side.

Working with Editors in Chief, the ED will develop audience growth plans, manage a small team, and ensure systems and policies support a healthy, inclusive workplace and strong community partnerships.

Qualifications

• Strong leadership and management experience guiding a team.
• Experience fundraising for nonprofits.
• Experience managing budgets and financial controls.
• Excellent written and verbal communication.
• Ability to build relationships with funders and Board.
• Commitment to community journalism in Chicago.
• Humility, patience, and willingness to learn.

Responsibilities

• Lead and support all direct reports including leadership meetings and reviews.
• Partner with EICs to implement healthy workplace culture.
• Oversee hiring, onboarding, and staff development.
• Implement shared systems across both publications.
• Develop and execute fundraising, revenue growth, grants.
• Manage budgeting, payroll, expenses, and internal controls.
• Engage with the Board and external partners to advance goals.

Skills

Leadership experience

Fundraising

Budgeting

Strategic planning

Communication

Team management

Board collaboration

Nonprofit funding

Job description

South Side Media Works (SSMW) is the nonprofit home of two community publications: the South Side Weekly and the Hyde Park Herald.

South Side Weekly, founded in 2013 with an all-volunteer staff, is a newsprint magazine dedicated to producing local journalism that is for, by, and about the South Side of Chicago. In 2022, the Weekly merged with the Hyde Park Herald, the oldest neighborhood newspaper in Chicago, which has covered Hyde Park and the South Lakefront since 1893. The Herald covers neighborhood events and local politics and is published weekly in print and near-daily online. With a staff of 8 and a large network of freelance contributors, the papers reach tens of thousands of readers each week with award-winning original reporting on politics, education, housing, the arts, and more.

Both publications are dedicated to developing emerging journalists and storytellers through strong editorial mentorship and accessible opportunities for emerging journalists to practice their craft. Former editors and writers have gone on to work for local outlets like Block Club Chicago, the TRiiBE, WBEZ, and the Chicago Reader, as well as national outlets like the Washington Post and the New York Times.

The Opportunity

South Side Media Works is planning for the future while navigating a critical moment for our work and local journalism at large. After a decade of growth, and on the heels of a historic merger, we believe the next phase of our organizational history will be transformational. We are looking for an Executive Director who is excited to build .

The Executive Director will manage all of the organization's publishing operations. They will lead the development of our annual budget and be accountable for funding it through subscriptions, advertising, individual donations, grants, and circulation revenue. In partnership with our editorial leadership, the Executive Director will be responsible for designing a clear strategy for reaching and growing our audience. They will ensure the team has clear goals and support, that our administrative systems run smoothly, that our partners and funders are engaged, and that the Board of Directors is fully equipped to advise and support. We seek a leader ready to step into a moment of dynamic strategic thinking and turn it into an innovative and achievable plan to support community journalism on the South Side of Chicago long into the future.

Qualifications

Note: This role—and the field of local publishing—requires a wide range of skills, and strong candidates may have most, but not all, of the qualifications below. If you see your work reflected strongly in at least half of these criteria, we strongly encourage you to apply. Our team and Board of Directors are ready to provide intentional support and professional development to the right candidate.

• You care deeply about local civic and cultural institutions, understand the power that local journalism can have on the lives of everyday Chicagoans, and are excited to remind and inspire others of the power of our mission.
• You love creating new systems and processes that make strategic goals come to life.
• You have extensive experience with both organizational leadership—defining and implementing strategy—and management—guiding a team to achieve results.
• You are familiar with nonprofit fundraising and have successfully fundraised for an organization or project. (Knowledge of the Chicago fundraising landscape is a significant plus.)
• You have significant hands-on experience managing an organizational budget and get energy from a great spreadsheet.
• You are a compelling communicator, unafraid to make asks, and skilled at motivating people to contribute their time, talent, and treasure to causes you believe in.
• You practice humility, patience, and continuous learning.
• You have personal connections and commitments to the South Side of Chicago that make you excited to support journalism and storytelling here.

Role & Responsibilities

The Executive Director is a full-time, exempt role reporting to the Board of Directors.

Organizational Leadership

• Manage and support all direct reports. This includes consistent check-ins and performance evaluations. The ED currently supervises four staff members: Editor in Chief of South Side Weekly, the Editor in Chief of Hyde Park Herald, our Advertising Manager, and our part-time Office Manager.
• Facilitate regular leadership meetings, attend editorial leadership meetings as needed, and maintain a close relationship with the Board of Directors so that communications and strategies can be facilitated across teams.
• In collaboration with both EICs, develop and implement practices that foster a healthy, supportive, and equitable workplace culture.
• Oversee hiring and onboarding of new employees and core contractors, in collaboration with each Editor in Chief.
• Lead the implementation of shared systems and processes across both publications, such as project management tools, audience reporting, and shared communication tools.
• Collaborate with the Board of Directors on strategic goals and provide monthly updates.

Development & Revenue

• Create and implement the organization's annual fundraising plan and core strategies for revenue growth.
• Partner with the Advertising Manager and Board of Directors to grow advertising revenue and develop subscription and membership strategies.
• Maintain relationships with key funders and take the lead on all grant proposals and reports.
• Actively prospect for new sources of revenue, including creating a more robust individual giving program and identifying new institutional funders.

Finance & Operations

• Administer HR-related duties including running payroll, paying contributors, approving expenses and PTO, and maintaining other organizational policies. Serve as point of contact for all major vendors and distributors.
• Lead the annual organizational budgeting process.
• Maintain financial controls and best practices, including completing the annual audit and improving current bookkeeping practices.

Board Partnership and Strategic Planning

• Work with the Board of Directors and Editorial Leadership to develop clear, measurable goals with achievable work plans.
• Work with each EIC to design the long-term audience and editorial strategy of each publication in line with the organization's mission and strategic goals.
• Regularly report to the Board of Directors on fundraising and revenue, staff, and operational issues.
• Collaborate with the Board Chair on agendas.
• Support board development through board member recruitment, committees, and board goal setting.

External Relationships

• Serve as the lead ambassador for the organization. Clearly communicate the organization's mission, values, and strategic vision to staff, community, funders, and audience.
• Represent South Side Media Works in stakeholder meetings, funder conversations, and speaking engagements.
• Identify partnerships that meet strategic priorities and support editorial leadership.

Compensation and Benefits

This position pays an annual base salary of $75,000 to $80,000. Benefits include monthly health insurance reimbursement, flexible work schedule, 30 PTO days, and 5 health days. Some in-person work hours at our office in Woodlawn will be required.

How to Apply

Please complete this application https://bit.ly/ssmwed by September 8, 2025 (11:59 CDT). Applications will be reviewed on a rolling basis.

South Side Media Works is an equal opportunity employer. We strongly encourage applications from people of color, women, LGBTQ+ candidates, and people with deep ties to the South Side and the communities we cover.