Executive Director, Technology Support

Chicago Public Schools (CPS) is one of the largest school districts in the United States, serving over 320,000 students in 600+ schools and employing approximately 40,000 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. In order to fulfill this mission, we make three commitments to our students, their families, and all Chicagoans: academic progress, financial stability, and integrity. Six core values are embedded within these commitments - student-centered, whole child, equity, academic excellence, community partnership, and continuous learning.
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 Officer, the Executive Director of Technology Support is responsible for the district-wide strategy and delivery of school and administrative end-user Technology Support functions. This position leads a team of directors and managers charged with delivering high-quality, cost-effective Technology Support services for one of the nation's largest school districts. Functional oversight includes the District technology service desk, the enterprise technology stabilization and support team, enterprise device systems and deployment, technology asset management and purchasing support, field support services for schools, and all supporting service-related applications. The Executive Director of Technology Support partners with our academic chiefs, schools, administrators, supporting staff, and strategic technology vendors to define the District's end-user Technology Support strategy, long-term technology roadmaps, device lifecycle management, key initiatives, adoption methodologies, and operational support procedures.
The Executive Director of Technology Support will be held accountable for the following responsibilities:

• Provide leadership and oversight of School Technology Support and Shared Services, including the District Technology Service Desk, the District Device Engineers Support Team, the District Technology Support Team, Functional Device Support Organizations, and a pool of field support vendors that support schools, in addition to daily collaboration with school technology coordinators (TechCOs).
• Define the end-user Technology Support strategy and long-term technology roadmap, and provide guidance and direction to a team of directors and managers responsible for each of these functions.
• Analyze customer feedback and support data to identify trends and patterns that can be addressed through the support strategy, and oversee the implementation of effective solutions.
• Effectively manage support vendor partners, including addressing issues/concerns raised by our constituents, utilizing industry-standard key performance indicators to continuously evaluate service levels, and leveraging cost and customer satisfaction metrics to deliver the right services and service levels.
• Recruit, onboard, and coach staff to ensure robust learning and career development consistent with the District's values and mission.
• Develop a high-performing and service-oriented culture within the team, in alignment with the broader technology team goals, and provide opportunities and a framework for team members' career growth and advancement.
• Maximize recent investments in demand management, portfolio management, mobile device management, and service desk software by operationalizing processes to manage demand and maintain an organization-wide knowledge base.
• In partnership with district and ITS leadership, establish policies and practices to ensure third-party invoices, timesheets, work orders, projects, and random audits are completed to meet CPS's Office of Ethics and Code of Conduct, in alignment with district policy and procedure.
• Build strong relationships with key stakeholders to develop department and school-specific Technology Support solutions and deliverables, and increase customer satisfaction.
• Create and manage department budget exceeding $40M per year, inclusive of Board Approval Process (BAP) items, personnel, other non-personnel operating, strategic support vendors, staff augmentation contractors, and capital funding.
• Other duties as assigned.

In order to be successful and achieve the above responsibilities, the Executive Director of Technology Support must possess the following qualifications:
Education Required:

• Bachelor's degree in a relevant field from an accredited college or university
• Master's degree preferred
• Relevant professional certifications/designations such as Project Management Professional (PMP), IT Infrastructure Library (ITIL), and expertise in Microsoft, Google, and Apple device platforms

Experience Required:

• Minimum of eight (8) years of relevant professional leadership experience in IT School Technology, IT Service Desk, IT Support Services, or IT Device Deployment, including the following, is required:
• Minimum of eight (8) years of experience leading/managing one or more of the above functions, including experience designing, developing, and leading a large (ex: 20 employees or more, 150 contractors or more, indirect 180 union employees or more) team of employees spanning multiple levels, including contractors, and management-level roles
• Experience in Senior-level IT service management, customer service management, and business functional service desk experience at a large, public or private sector institution similar in size and complexity to Chicago Public Schools, preferred
• Minimum of fifteen (15) years of the experience above, strongly preferred

Other Requirements:

• Local and Domestic travel (E.g., traveling to different CPS locations, attending Google, Apple, and Microsoft TechEd conferences, etc.) required up to 10%.

Knowledge, Skills, and Abilities:

• Strong verbal and written communication skills, including the ability to facilitate presentations to technical and non-technical audiences
• High levels of IT expertise, integrity, honesty, credibility, and the courage to make difficult yet necessary decisions
• Ability to work in collaboration with the ITS leadership team to understand and adhere to CPS ITS strategies, standards, and policies
• Ability to develop deep knowledge of 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
• Ability to define problems, analyze data, and outline valid conclusions and action steps
• 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

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.
• Be Fully Vaccinated Against COVID-19 - Unless approved for a medical or religious exemption, all employees are required to be up-to-date on COVID-19 vaccinations, including boosters, and to submit proof of vaccination to the district within 30 days of hire. "Up-to-date" on vaccination is defined as being at least two weeks past all primary vaccine doses and any applicable boosters.