Deputy Chief, Information and Technology Services

Job Title: Deputy Chief Information and Technology Services

Job Number: 260000C1

Date: Mar 11, 2026

Time: 30:58 PM

Location: Central-42 West Madison Street, Information & Technology Svcs

Job Summary:

Reporting to the Chief Information & Technology Officer (CIO), the Deputy Chief of Information and Technology Services (ITS) is responsible for overseeing the successful execution of IT-related initiatives that strengthen district-wide IT services while enabling CPS to operate more efficiently.

About Chicago Public Schools (CPS)

Chicago Public Schools (CPS) is a district on the rise, serving over 325,000 students in 500 schools and employing over 45,000 people, most of whom are teachers. CPS has set ambitious goals to ensure that every student in every school and every neighborhood has access to a world-class learning experience that prepares each for success in college, career, and civic life.

Core Values:

Six core values guide the work we do every day for our students:

1. Student-centered
2. Whole child
3. Equity
4. Academic excellence
5. Community partnership
6. Continuous learning

About the Office of Information and Technology Services (ITS)

The Office of Information and Technology Services (ITS) works to build the capacity of schools to use information and technology, maintain network infrastructure security standards, and support other departments to meet district goals. ITS provides innovative technology solutions that improve the quality of education for students, reduce the administrative burden on educators, facilitate parent interaction, increase community engagement, and support CPSs mission of transparency by focusing on the ease and equity of access to information.

Responsibilities:

The Deputy Chief of ITS will be held accountable for the following responsibilities:

• Provide Organizational Vision, Advising, and Strategic Planning
• Serve as the organizational lead in the areas of IT strategic direction, organizational effectiveness, contract, and vendor management, administration, finance, and department-wide communications
• Advise the CIO and function with high-level decision-making authority on behalf of ITS and the CIO
• Collaborate closely with the CIO to develop and implement the ITS organizational vision and strategic and operational plans, aligning IT priorities and actions in support of District-wide goals
• Oversee and provide guidance on numerous ITS cross-department initiatives to ensure collaboration, financial planning, and project delivery
• Advise ITS department leaders, offering guidance and providing organizational perspective on departmental planning efforts, remediating escalated issues as needed
• Serve as an escalation point for 3rd party vendors and collaborate as needed to enhance services based on user evaluations and other quality measures
• Assist with the development and communication of processes for valuing IT services
• Develop, propose, enhance, and execute on IT-related initiatives that will strengthen District-wide IT services and increase organizational efficiency
• Manage Infrastructure Operations, Planning, and People
• Provide direct management and oversight to ITS functions and teams, including but not limited to:
• Network Services
• Client Systems
• Telecommunications Services
• Enterprise Server Operations
• Supervise, develop, and manage the performance of employees across multiple teams and functions
• Ensure Infrastructure functions and teams are aligned to ITS strategic and operational plans and meet the necessary functionality, quality, customer service, and skill-competency requirements for success
• Drive and oversee ITS financial planning and strategy, maintain accountability for the organizations operational budget, encouraging ITS leadership to identify opportunities for cost savings as a practice
• Provide direct oversight over staffing changes and requests, ensuring resources are justified and best aligned with services that advance organizational goals in support of CPS needs
• Contribute to and support the departments people priorities and objectives regarding people leader effectiveness, engaging employees, and enabling others to perform
• Manage ITS Senior Staff meetings and chair the meeting in the absence of the CIO or as otherwise requested
• Recruit, onboard, and coach staff to ensure robust learning and career development consistent with CPSs values and mission

Strategic Governance Council Leadership Board Briefings and Budget Planning:

• Staff the ITS Strategic Governance Council (ITSGC) working closely with executive leadership to anticipate and plan for future ITS needs over multiple years, assisting in portfolio prioritization and the allocation and management of CPS information systems, ITS Annual Fund, and IT Capital Fund
• On behalf of ITS, manage the monthly CPS Board of Education Briefing process, Public Briefing, and presentations to the Board of Directors
• Represent ITS in Internal and External Collaborations
• Coordinate a variety of ITS cross-functional teams enabling continuous improvement, guiding the identification of goals and objectives, and monitoring progress toward deliverables
• Establish, enhance, and maintain effective relationships and communication with all CPS constituents, community stakeholders, regional, and national IT associations, and vendors
• Establish communication channels and other resolution mechanisms to maximize desired results and minimize any potential conflict
• Represent ITS on a variety of District-wide and/or C-level committees and enterprise governance councils
• Consult with external technology experts to identify emerging IT trends and opportunities and evaluate them within CPS and ITSs strategic direction

Requirements:

• Education: Bachelors Degree in Computer Science, Information Technology, Business Management, Infrastructure Engineering, Project Management, or a related field from an accredited college or university is required
• Masters degree in Business Administration, Information Systems, or related advanced degree is preferred
• Relevant professional designations/certifications such as:
• IT Infrastructure Library (ITIL)
• Project Management Professional (PMP)
• Enterprise Resource Planning (ERP) certifications
• Cisco Certified Network Associate (CCNA)
• Cisco Certified Network Professional (CCNP)
• CompTIA Network
• ISC2 Certified Secure Software Lifecycle Professional
• Experience: Minimum of ten (10) years of professional IT leadership experience in enterprise resource planning, infrastructure, cybersecurity, and operations, including:
• Minimum of five (5) years of formal leadership experience in a manager/supervisor role leading a team of direct reports within a complex IT organization
• Experience within a large urban K-12 school district or Higher Education setting is strongly preferred
• Minimum of twenty (20) years of experience above, including seven (7) or more years of IT leadership and/or senior leadership experience preferred

Knowledge, Skills, and Abilities:

• Excellent interpersonal, verbal, and written communication skills, including the ability to facilitate presentations to senior-level professionals, technical, and non-technical audiences
• Ability to develop deep knowledge of IT in a K-12 education environment as well as the Districts business units and functions, building both horizontal and vertical relationships with business departments and IT leaders that deliver business impact
• Strong leadership and team building skills, e.g., ability to develop high-performing teams united around a clear vision for serving schools and achieving student success
• Expertise in leadership development, ability to coach directors and managers toward excellence and build the capacity of technical teams
• Ability to contribute to the people priorities and objectives regarding people leader effectiveness, employee engagement, and enabling others to perform
• Ability to articulate a vision, set high standards, and effectively guide teams and stakeholders in the realization of expectations set
• Effective strategic planning capabilities, including the ability to establish long-term vision and goals and align/manage activities toward goal fulfillment
• Knowledge of operations budget/finance management and organizational development
• Ability to build collaborative relationships with a variety of constituent groups, including external partners, to ensure the entire system operates in the most effective manner possible to support organizational success
• High levels of IT expertise, integrity, honesty, credibility, exceptional judgment, and the courage to make difficult yet necessary decisions
• Familiarity and a thorough knowledge and understanding of IT management, infrastructure operations, and service delivery across multiple business areas
• A broad range of IT products and services
• Ability to define problems, analyze data, and outline valid conclusions and action steps
• Strong understanding of the ways IT decisions may impact operations, ability to advise on the potential outcome of critical decisions, develop and implement strategies for communicating these decisions, and achieving desired results
• Commitment to diversity, equity, inclusion, and serving the needs of a diverse School-district community
• Capable of following Company policies and practices while representing CPS in an ethical and professional manner in all interactions with employees, governmental agencies, vendors, contractors, suppliers, students, and the Chicago community
• Skilled in the use of Microsoft Office, Word, Excel, PowerPoint, and Google Workspace

Benefits:

• Health & Wellness: Your Care Your Choice
• Financial Security: Planning for Today and Tomorrow
• Work-Life Balance: Supporting Your Personal and Professional Life

Conditions of Employment:

• As a condition of employment with the Chicago Public Schools (CPS), employees are required to:
• Establish/Maintain Chicago Residency: Employees are required to live within the geographic boundaries of the City of Chicago within six months of their CPS hire date and maintain residency throughout their employment with the district.
• The Chicago residency requirement does not apply to temporary/part-time positions; however, all CPS employees must be residents of Illinois.