On Monday, July 25, teams from the Herald and South Side Weekly gathered to take a photograph commemorating the merger. Photo by Marc C. Monaghan
Photo by Marc C. Monaghan

Lead a creative and collaborative team that believes in producing media that centers the needs and voices of South Siders

About South Side Weekly NFP

Founded in 2013, South Side Weekly NFP is a nonprofit newsroom dedicated to producing local journalism that is for, by, and about the South Side of Chicago. 

Over the past decade, the Weekly has grown from a volunteer-run newsroom to a nonprofit with eleven employees and a large network of freelance contributors. In 2022, the Weekly merged with the Hyde Park Herald, the oldest community newspaper in Chicago. Together, the papers reach tens of thousands of readers each week with award-winning original reporting on politics, education, housing, the arts and more.

South Side Weekly NFP is also dedicated to supporting and developing emerging journalists and storytellers through a variety of training opportunities including free workshops and an editor training fellowship. Former contributors 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

Job Description

We are seeking a passionate and experienced executive director to lead our growing team of ten staff members and dozens of contractors. The executive director will be responsible for overseeing the strategic vision, financial sustainability, and day-to-day operations of the organization. This is a broad role that touches on every aspect of the organization’s work, but the three clear priorities are fundraising, managing and supporting a team, and strategic planning. This is a full-time, salaried position that reports directly to the Board of Directors.

In this role you will lead a creative and collaborative team that is committed to producing high-quality news in partnership with communities on the South Side. You will be responsible for the management of people and resources necessary to efficiently operate, responsibly grow, and broaden the reach and impact of our organization. Our ideal candidate will be detail-oriented, organized and have a proven track record of working collaboratively with team members.

While you will not be directly responsible for making editorial decisions, you will work closely with editorial leadership across newsrooms to assist in the development and execution of reporting projects and training programs to serve our growing network of readers and contributors. 

This is a multifaceted role that requires a highly-driven and compassionate leader who can motivate and support the Weekly’s growing team.

The executive director will be responsible for:

  • Managing and supporting all direct reports to success in their roles 
  • Working with the board of directors and editorial leadership to develop and implement strategic goals 
  • Facilitating communication across teams and making sure staff and contractors are kept in the loop about strategic goals 
  • Leading organizational budgeting process, approving expenditures, and running payroll
  • Working with bookkeeping firm to produce quarterly financial reports and accounting firm to file tax returns and conduct a yearly audit
  • Ensuring that the organizations physical and technological infrastructure is sufficient for staff use and program goals 
  • Managing organizational risk through regular analysis, updates to policies, and insurance
  • Taking lead on writing foundation grant proposals and reports
  • Developing and implementing fundraising strategies for small and large donors
  • Working with the Advertising Manager to develop and implement advertising strategies
  • Working with the Office Manager to develop and implement subscription strategies
  • Overseeing the hiring and onboarding of new employees and contractors 
  • Working in collaboration with editorial leadership to develop, implement, and evaluate practices that foster a healthy and supportive workplace culture
  • Representing the organization through stakeholder meetings and speaking engagements
  • Reporting back to the the board of directors with regular updates on budgeting, fundraising, staffing, and operations

We expect that the strongest candidates will have the skills and areas of expertise listed below in varying degrees. If you don’t have every qualification, please consider applying, and use your application to tell us about the skills you have to help us build our team.

  • Management or leadership experience
  • Experience managing an organizational budget
  • Fundraising experience, or willingness to learn
  • Excellent written and oral communication skills
  • Excellent organizational skills with proven ability to prioritize and implement
  • Experience working collaboratively with a team to achieve strategic goals 

Reports to
The Board of Directors

Direct Reports
South Side Weekly’s Editor-in-Chief
South Side Weekly’s Managing Editor
Hyde Park Herald’s Editor-in-chief
Special Projects Coordinator
Office Manager
Advertising Manager
Production Manager

Time Commitment
This is a full-time exempt position at 40 hrs/week starting on July 1, 2023. This is a hybrid work position that will require you to work from the Weekly’s office, located at 6100 S Blackstone Ave in Woodlawn, at least 1-2 days a week. 

Compensation & Benefits
Flexible work schedule
10 vacation days
Winter break between Christmas and New Years
20 days of paid time off 

Application deadline
Monday, June 5 at 11:59PM

Apply here