Director of Strategy and Operations
Job Type

The Chicago Sun-Times is the hardest-working paper in America, covering the stories and issues that matter most to Chicagoans with depth, integrity, and grit. The newsroom has earned eight Pulitzer Prizes for its hard-hitting investigative reporting, in-depth political coverage, insightful sports analysis, entertainment reviews, and cultural commentary. An industry-leading innovator in local news, it has been recognized nationally for expanding digital and multimedia reporting platforms alongside its indomitable newspaper, the oldest continuously published daily in the city.

In January 2022, the Sun-Times merged with public radio station WBEZ with a shared mission to strengthen local journalism in Chicago. Under the banner of Chicago Public Media, Chicago Sun-Times Media, Inc. (CSTM) is now part of one of the largest nonprofit news organizations in the nation. This merger reinforces our commitment to serving Chicagoans with the news that matters most -– fact-based, unbiased journalism that is deeply connected to Chicago communities.

An Opportunity to Make an Impact

We are looking for a Director of Strategy and Operations who can be part of a newsroom in one of the most exciting and diverse metropolitan areas in America.  We are looking for a leader who can plan and collaborate across the newsroom and larger organization, bringing order, inclusivity, and nimbleness to everything we do.


  • Rethink and improve newsroom operations and processes, working closely and collaboratively with the rest of the newsroom and cross-functional teams.
  • Establish a better newsflow for creating, posting, and publishing content, including setting deadline standards for submitting copy, images, or art for all platforms, both for breaking news, enterprise, and long-term stories.
  • Develop a robust forward planning strategy that can be integrated into the newsroom processes and workflow.
  • Set goals and establish sensible metrics for success, working with leadership across the organization; and working with analytics and audience team members to ensure we are making data-led decisions in our daily coverage, goal setting, and editorial strategy.
  • Manage the financial budget for the newsroom editorial budget (financial) and communicate budget expectations to different stakeholders.
  • Lead strategic initiatives across the newsroom to help the Sun-Times meet its key goals, including growing editorial impact, reputation, revenue, membership, audience and community engagement, and service.
  • Train and develop the newsroom, working closely with the deputy managing editor, DEI, and administration.
  • Transition the newsroom to be more audience-and digital-first, instilling innovation across all of our platforms and formats. 
  • Liaise with teams across the Sun-Times and Chicago Public Media, including marketing, circulation, product, digital, and revenue teams, ensuring we are successfully collaborating to serve readers, innovate and meet our short- and long-term goals.
  • As part of the editorial leadership team, help maximize the quality and impact of the journalism we're delivering to meet our community’s needs, in line with the editorial vision set by the executive editor.

Preferred Skills:

  • Bachelor’s degree in journalism, communications, or related training.
  • More than five years of media management and editing experience.
  • Strong communication skills.
  • Strong people-management skills.
  •  Strong problem-solving skills.
  • Ability to react quickly in a deadline-driven environment. 
  • Ability to balance a mix of short-term and long-term projects and work collaboratively both within cross-functional newsroom teams and with our partners.

What We Offer

  • A competitive salary and benefits package which includes medical, dental, vision, life insurance, disability coverage, retirement savings, FSA plan including a commuter benefits plan
  • Opportunity to work within a collaborative team culture
  • A flexible work schedule
  • Opportunity to be part of an iconic brand
  • This a unique opportunity to lead an influential local news outlet in an innovative, exciting market at a time when it has joined Chicago Public Media, become a nonprofit, and adopted a membership model without a paywall.

The information contained in this job description is not intended to create any contractual or other legal commitment. CSTM may change the content or format of this job at any time at its sole and exclusive discretion without notice. This role does not offer sponsorship employment benefits.

CSTM does not discriminate in its employment decisions based on race, ethnicity, gender, sexual orientation, religion, age, disability, citizenship or national origin, veteran status, or on any other basis which would violate any applicable federal, state, or local law.