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Chicago Public Schools (CPS) is one of the largest school districts in the United States, serving over330,000students in 600+ schools and employing nearly 36,000 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 Department 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: 

The Executive Director of Enterprise Application Services is responsible for the management of CPS enterprise applications, inclusive of the following domains: Student Information, ERP Finance Budgeting, ERP Human Capital Management (HCM), Web Systems and Service Management.  This purview also includes management of the primary CPS website (CPS.EDU) and a host of other custom applications.  This position will have a supervisory scope that includes resources overall with direct reports, including FTE and consulting staff.  Administrative responsibility entails management of a $15-30M budget, multiple vendor relationships, and related contractual agreements.

The Executive Director, Enterprise Application Services will be held accountable for the following responsibilities:

• Develop long-term strategic planning for all CPS IT application tiers (personal, transactional, analytic); Ensure decreased investment in depreciable hardware and an increased emphasis on cloud technologies.
• Develop and implement a strategy for reducing the complexity of information systems in a cost-effective manner, for example by decreasing the number of applications or moving away from legacy systems.
• Define the architecture, security, and technology standards for all applications and infrastructure across the organization, and ensure those standards are published, updated, and made widely available.
• Personally responsible for performance reviews of direct reports, staff calibration, talent reviews, compensation proposals, and the timely completion of all  Talent/HR deadlines for the larger enterprise application footprint.
• The fulfillment of critical, mission-aligned training and professional certification opportunities for key enterprise application staff members.
• Inspire staff by the implementation of tangible processes leading to increased employee engagement, development, retention, and succession planning for key positions.
• Oversee, monitor, and report progress on complex and/or multiple projects relative to schedules, budgets, scope, and quality.
• Coordinate and track work across teams in the organization to achieve project deliverables and goals.
• Ensure that all locally developed and vendor-based application changes consistently follow a Best Practice software development life cycle (SDLC), scaled agile framework (SAFe), and adhere to local standards set forth by the ITS change manager, Change Control Board (CCB), and Architecture Review Board (ARB).
• The creation of a centralized IT software development team (COE or Shared Services model), ensuring consistency of approach and cross training relative to the support of the various application verticals.
• Assess and communicate the impacts, trade-offs, risks, costs, benefits, and opportunities of IT solutions.
• Establish a formal client engagement framework for each application specialty, ensuring mission alignment, proper prioritization of tasks and generally building customer awareness.
• Collaborate closely with business and technology partners to assure transparency and consistent direction in development priorities.
• Personally providing project leadership, including work direction and feedback to the sponsors, project leads, and teams for high priority ITS initiatives.
• Negotiating and resolving conflicting change requests and changing priorities across customers/projects. Facilitating solutions to complex problems.
• Building high quality working relationships with executives, technology partners, customers, and all other relevant individuals and groups.
• Partner with Procurement to ensure that the services and performance of major partners are examined through a quarterly business review.
• Serve as a final reviewer/editor for all application focused vendor contracts.
• Direct responsibility for negotiation of application-based vendor contracts.
• Hold vendors accountable for general performance and service levels.
• Ensure the ITS enterprise application budget is tightly managed and not exceeded.
• Quality assurance of all application related proposals and submissions to the CPS Board of Education.

In order to be successful and achieve the above responsibilities, the Executive Director, Enterprise Application Services must possess the following qualifications: 

Education Required: 

• Bachelor’s degree in a relevant field from an accredited college or university

Experience Required: 

• Minimum of 10 years of relevant enterprise applications, cloud-based solutions, and ERP deployment experience, required
• Minimum of ten (10) years of experience with application development, enterprise architecture, and management of multiple application teams in a large enterprise environment or center of excellence (COE), required 
• Minimum of fifteen (15) years of the above experience, strongly preferred
• Experience implementing cloud-based software platforms such as Google Apps, Microsoft Azure, and Amazon AWS, required
• Experience with multiple database types, required
• Experience balancing and leading the prioritization of new project efforts, required
• Experience implementing open-source software, preferred
• Project Management Professional (PMP), Program Management Professional (PgMP), or Certified Scrum Master (CSM) certification, is preferred 

Knowledge, Skills, and Abilities:

• Excellent verbal and written communication skills, including the ability to advise technical and non-technical stakeholders on technical topics (ie: online data collection, useful reporting tools, etc.) in an understandable manner in order to support usability 
• Effective project management and strategic planning capabilities, including the ability to establish long-term vision and goals, and align/manage activities toward goal fulfillment
• Excellent organization, prioritization and time management capabilities, including the ability to manage and lead teams through multiple complex projects simultaneously, driving them to completion and achieving success
• Capable of success in a fast-paced environment; ability to anticipate the short- and long-term demands of stakeholders, proactively consider solutions, and maintain flexibility to meet the changing needs of the organization
• Ability to articulate a vision, set high standards, and effectively guide stakeholders and team members in the realization of expectations set
• 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 build collaborative, cross-functional relationships with a variety of constituent groups, including technical and non-technical stakeholders and external partners, to ensure the entire system operates in the most effective manner possible to support organizational success
• Exceptional problem-solving skills; ability to define problems, analyze data, and outline valid conclusions and action steps; proactive, decisive, action-oriented individual 
• High levels of attention to detail, IT expertise, integrity, honesty, credibility, and the courage to make difficult yet necessary decisions
• Familiarity with the establishment of data schemas and taxonomies 
• Ability to deliver reports and online tools in a fast-paced environment, respond immediately to multiple constituencies, and meet established deadlines
• Familiarity with Best Practice standards for managing a Software Development Life Cycle (SDLC), Scrum, or Scaled Agile Framework (SAFe)
• Working knowledge of several of the following tools: Microsoft.NET, ASP.Net 4.5, MVC 4, Web Forms, C#, Angular, JavaScript, jQuery, Twitter Bootstrap, JSON, Mobile Web Development, Responsive Design Frameworks, REST, HTML5, CSS3, XML, SQL, Oracle 11i, SQL Server 2012, Windows 2012, Relational Databases, object-oriented analysis/design, Rapid Application Development, Web Services, Continuous Integration, Version Control tools such as Git, Subversion or Team Foundation Server.
• Proven ability to troubleshoot and debug existing software systems
• Must be familiar with the principles of project management, including but not limited to experience with both Waterfall and AGILE project management methodologies 

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.