Director of Advertising Technology and Operations

The Director of Advertising Technology & Operations leads the IT function that supports Lee Enterprises’ advertising business. The role is accountable for the reliability and direction of advertising platforms, integrations, and technical operations spanning sales and order entry, digital fulfillment, creative and print production, billing and payments, and reporting.

The Director leads technical staff, sets priorities across daily support and change initiatives, and serves as a primary IT partner to Advertising leadership. Working with Finance, Sales Enablement, Product, Application Development, Infrastructure, Security, the PMO, and vendors, this position turns business needs into practical technology plans and provides leadership for major implementations and migrations.

Supervisory Responsibilities:

Directly supervises and develops the platform support analysts and other technical staff assigned to Advertising Operations. Sets individual and team priorities, allocates work, manages performance, plans coverage and succession, and supports staff development.

Core Responsibilities: 

• Own the IT strategy and operational performance of advertising order management, CRM and sales workflows, creative and production systems, digital advertising, payment processing, reporting, and related third-party platforms.
• Directly lead the platform support analysts and other assigned technical staff; establish priorities, allocate capacity, develop employees, and maintain support coverage and institutional knowledge for critical systems.
• Partner with Advertising and IT leadership to translate business requirements into technology roadmaps and a prioritized Jira backlog, balancing operational support, enhancements, and project delivery against available capacity.
• Oversee application support, incident escalation, problem resolution, upgrades, change management, and operational readiness for revenue- and production-critical systems.
• Lead the technical and operational aspects of platform implementations and migrations, including requirements, testing, cutover, stabilization, and transition or retirement of legacy systems.
• Oversee integrations and data flows among order management, CRM, digital fulfillment, creative and pagination systems, billing, payments, and reporting; establish priorities for configuration, automation, and enhancements.
• Ensure system changes are tested across connected workflows and validated with business users, including production checks and reconciliation where transactions affect financial records.
• Partner with Finance on advertising billing, accounts receivable, payments, reconciliation, and controls at the points where advertising and financial systems meet.
• Coordinate with development, architecture, infrastructure, security, and service management teams to resolve issues and align platforms with enterprise standards.
• Manage advertising technology vendor relationships, including escalations, implementation commitments, service performance, technical requirements, and product direction.
• Maintain operational documentation, access governance, audit support, business continuity, and disaster recovery practices for advertising systems.
• Use Jira and a regular Agile planning and review cadence to track commitments, completed work, blockers, and dependencies; report delivery progress, system health, risks, and resource needs to IT leadership and business stakeholders. Coordinate timely response to critical issues, including after-hours escalation when necessary.

Preferred Skills & Experience:

• Experience leading enterprise applications and technical teams in a complex, integrated operating environment.
• Ability to direct work across application support, systems analysis, integrations, production technology, and software development disciplines.
• Working knowledge of APIs, data exchanges, automation, vendor-hosted platforms, and the controls needed to support reliable cross-system processes.
• Experience leading major implementations, migrations, upgrades, and vendor relationships while balancing ongoing support needs.
• Ability to use Agile practices and Jira to manage a transparent backlog, guide planning and delivery reviews, and communicate progress and technical risks to engineers, vendors, business partners, and senior leaders.
• Advertising, media, order management, CRM, digital fulfillment, payment, or production systems experience preferred; familiarity with Naviga Ad, Adbase, HubSpot, Google Ad Manager, or related platforms is an advantage.

Education & Experience:

• Bachelor’s degree in information technology, computer science, business, or a related field preferred; equivalent relevant experience may be considered.
• Eight or more years of progressive experience in IT, enterprise applications, business systems, or related work, including at least three years leading technical teams or major technology programs.
• Experience supporting integrated systems in a multi-location or enterprise environment preferred.