Deputy Chief, Information and Technology Services

Chicago Public Schools•Chicago, IL

About The Position

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 them 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. Aligned with our transformed philosophy, we are steadfastly focused on ensuring that the District provides resources equitably to support every student, every school, and every community. Six core values guide the work we do every day for our students – student-centered, whole child, equity, academic excellence, community partnership, and continuous learning. Each role in the district supports our vision that every student deserves a rigorous, joyful, and equitable learning experience. 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 CPS’ mission of transparency by focusing on the ease and equity of access to information. Job Summary: Reporting to the Chief Information & Technology Officer (CIO), the Deputy Chief of 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. This position will provide leadership and expertise in areas including ITS enterprise management and operations, and will ensure the organizational effectiveness of infrastructure services. The Deputy Chief of ITS will lead and manage a team of highly motivated IT professionals, represent the CIO in times of absence, and will function as the ITS organization’s chief of staff.

Requirements

Bachelor’s Degree in Computer Science, Information Technology, Business Management, Infrastructure Engineering, Project Management, or a related field from an accredited college or university is required
Minimum of ten (10) years of professional IT leadership experience in enterprise resource planning, infrastructure, cybersecurity, and operations, including the following, is required:
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
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 District’s 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
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.

Nice To Haves

Master’s 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+, (ISC)2 Certified Secure Software Lifecycle Professional, preferred
Experience within a large, urban K-12 school district or Higher Education setting is strongly preferred.
Minimum of twenty (20) years of the experience above, including seven (7) or more years of IT leadership and/or senior leadership experience, preferred

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 organization’s 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 department’s 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 CPS’s 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 (E.g., Great City Schools, Oracle, Google, sister agencies, other PreK-12 educational institutions, etc.)
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 ITS’s strategic direction
Other duties and workstreams as assigned

Benefits

Health & Wellness: Your Care, Your Choice
CPS is committed to providing comprehensive health coverage to our employees and their eligible dependents. You'll have access to a variety of choices to best fit your needs:
Medical Plan Options
Pharmacy
Dental
Vision
Behavioral Health & EAP
Employee Wellness Program
Financial Security: Planning for Today and Tomorrow
We understand the importance of financial stability, which is why CPS offers strong retirement and savings options:
Basic Life Insurance
Life and Disability Insurance
Pension Plans
Supplemental Retirement Plans (403(b) and 457(b))
Flexible Spending Accounts (FSAs)
Spot Pet Insurance
Work-Life Balance: Supporting Your Personal and Professional Life
CPS values the well-being of its employees and offers competitive paid time off policies:
Paid Leave
Sick Leave
Vacation Days
Parental Leaves
Short-Term Disability
Religious Holidays
Leaves