Director of Enterprise Systems

About the Sun-Times

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 daily newspaper, which celebrated its 75th anniversary in 2023.

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.

The Opportunity

Chicago Public Media is seeking a Director of Enterprise Systems to lead the modernization, integration, and long-term strategy of the technology platforms that power our audience relationships and revenue growth. This role sits at the intersection of systems architecture, data strategy, operational design, and digital transformation — and is ideal for someone who can move fluidly between hands-on technical execution and high-level strategic planning.

You will help build and maintain the next generation of our CRM, eCRM, fundraising, subscription, and data systems — guiding the organization toward a unified, scalable, and future-ready infrastructure. You will be instrumental in reducing silos, elevating data maturity, and ensuring Chicago Public Media stays on the cutting edge of how we engage and serve audiences across both WBEZ and the Chicago Sun-Times.

General Responsibilities

Enterprise Architecture & Systems Integration

• Modernize and unify all CRMs, donor, subscription, and audience platforms.

• Develop a cohesive systems roadmap to streamline data flow across key departments (Membership, Development, Subscription, Marketing, Product).

• Act as a hands-on technical leader for scoping, troubleshooting, and building necessary integrations.

• Implement scalable architectural patterns, APIs, and automation for future-proof infrastructure.

Revenue Enablement & Operational Optimization

• Oversee the systems and workflows that power donations, memberships, and subscriptions.

• Reduce manual workarounds and operational bottlenecks; implement automation, data governance practices, and efficient processes that support revenue growth.

• Partner with Membership, Development, and Marketing teams to enable sophisticated segmentation, personalization, lifecycle marketing, and performance insights.

Audience Funnel & Lifecycle Strategy

• Collaborate with cross-functional leaders to reimagine the full audience journey — from new visitor to engaged member, donor, or subscriber.

• Build the data and systems foundations needed for lifecycle marketing, behavioral triggers, and multi-channel engagement.

• Translate strategic goals into actionable technical requirements that support acquisition, retention, and long-term audience value.

Leadership, Collaboration & Change Management

• Act as connective tissue across CPM’s brands and departments, fostering alignment around shared data, common tools, and unified operating practices.

• Manage our growing enterprise systems team of engineers and CRM specialists.

• Lead rigorous requirements-gathering and change-management processes to ensure systems improvements land smoothly and effectively.

• Establish technical and operational standards that raise the bar for how CPM evaluates, implements, and maintains enterprise systems.

• Mentor, coach, and support team members; model a leadership style that blends execution with strategic guidance.

Qualifications

• 5+ years leading enterprise systems, digital transformation, revenue operations, or systems architecture — ideally in mission-driven, media, or multi-stakeholder environments.

• Demonstrated expertise in CRM/eCRM platforms, fundraising and subscription technologies, and the integrations that bind them. Experience with Snowflake is a plus.

• Proficiency in SQL for complex data extraction, manipulation, and ensuring compliance with business rules.

• Proficiency with Python or similar languages for API integration and building data pipelines.

• Hands-on experience evaluating, selecting, implementing, and optimizing systems.

• Deep experience integrating tools across marketing, membership, development, and finance — with a clear point of view on how data should flow across teams.

• Strong grounding in data strategy: governance, segmentation, automation, reporting, analytics, and personalization.

• Proven ability to lead complex, cross-functional initiatives and influence outcomes without formal authority.

• Exceptional communication and strategic storytelling skills, with the ability to translate technical concepts into language that drives understanding and adoption.

• Comfort working in environments of ambiguity and change, with the ability to bring clarity and structure where needed.

• Curiosity and drive to keep Chicago Public Media at the leading edge of audience and revenue technology.

Compensation

The expected pay range for this position is $145,000 - $175,000.00 per ANNUM.

Chicago Public Media provides pay ranges representing its good faith estimate of what the organization reasonably expects to pay for a position. The pay offered to a selected candidate will be determined based on factors such as (but not limited to the scope and responsibilities of the position, the qualifications of the selected candidate, departmental budget availability, internal equity, geographical location, and external market pay for comparable jobs.

Working at Chicago Public Media

At Chicago Public Media, we care deeply about our employees as we know attracting, developing, and growing talent is key to our success and enhancing our impact.

Our culture is one where collaboration, diversity of ideas, and innovation are encouraged. We value colleagues who will enhance our culture by bringing new ideas, divergent experiences, and talents to our dynamic workplace.

At Chicago Public Media we believe dedication to a great workplace includes supporting our employees and their families. As a result, we provide a broad and generous benefits package for employees at hire and in the years to come.

Our benefits include a competitive salary and benefits package which includes medical, dental, vision, vacation, holidays, life insurance, disability coverage, retirement savings, and a commuter benefits plan.

Chicago Public Media is an Equal Opportunity Employer, and we actively seek and welcome people from all backgrounds, orientations, and life experiences to join our team.

The essential functions described above are not all-inclusive and are not intended to create any contractual or other legal commitment. Chicago Public Media may change the content or format of this job at any time in its sole and exclusive discretion without notice.