Head of Delivery

The City of Chicago - Department of Technology & Innovation is seeking a dynamic Head of Delivery to oversee our technology services and lead teams of technologists and business-focused staff. This senior-level role is pivotal in driving our city's digital transformation and delivering best-in-class technical services to our 30+ departments and stakeholders.

Deadline to submit applications is June 23, 2025.

Position Overview:

In this role, you will collaborate with the CIO and senior leaders to implement a service-oriented operating model. You will be responsible for creating and growing our IT Delivery practice, including:

• Overseeing resource allocation and project execution to ensure teams are equipped to achieve objectives.
• Championing best practices in software engineering, data science, and digital/web services.
• Guiding Business Relationship Managers (BRMs) to align services with the city s IT vision and strategic plan.
• Driving the transformation of the City s websites and mobile applications for enhanced user experiences.
• Leading the development of a robust data science practice using AI and analytics.
• Managing vendor relationships, project timelines, budgets, and deliverables.
• Recruiting, hiring, and developing top technical talent to foster a culture of success and innovation.

Key Responsibilities:

• Execute projects approved by the Technology Strategy Group, Head of Planning and/or as authorized by the CIO in an efficient and judicious manner
• Oversee software engineering to ensure successful solution outcomes; champion best practices, development standards, and ensure goals for code quality, maintainability, security, and scalability
• Oversees Business Relationship Managers assigned to departments who are expected to have a robust understanding of business and technical priorities in their portfolio; understand the project demand backlog and system modification needs, and guide prioritization based on the City s IT Vision and Strategic Plan
• Ensures solution alignment with the city s technology architecture; reduce technical debt by application rationalization and modernization and contribute to platform standardization goals
• Oversees systems integrators and project modernization plans for major application overhauls such as Enterprise Resource Planning (ERP), Customer Information Systems (CIS), and Inspections, Permit, and Licensing Systems
• Ensures that solutions are digital-first, accessible, equitable, and focused on the best user experience for employees, residents, businesses, and other stakeholders
• Works with service owners and technical architects to design, manage, and/or execute product roadmaps that meet the needs of the user departments, while keeping the enterprise-wide goals in perspective
• Establishes a robust and professional PMO that develops and manages project plans, timelines, budgets, and key deliverables throughout the project life cycle

Minimum Qualifications:

Education, Training, and Experience

Graduation from an accredited college or university with a bachelor s degree in information technology, Business, Computer Science, or a directly related field, plus ten (10) years of software engineering experience, or an equivalent combination of education, training, and experience.

MBA or master s degree, preferred

Licensure, Certification, or Other Qualifications

Applicable professional licenses or certifications relative to the specific responsibilities of the position may be required.

Why Join Us?

Be part of a forward-thinking team shaping the future of Chicago s technology landscape. Engage in impactful projects that enhance the lives of residents, businesses, and city employees. Enjoy a collaborative and inclusive work environment with opportunities for professional growth.

Apply now and help drive Chicago s digital transformation as our Head of Delivery! Send cover letter and resume to