IT Project Portfolio Manager

Chicago Public Schools (CPS) is a district on the rise, serving over 320,000 students in 500+ schools and employing over 44,000 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:

The Manager of IT Project Portfolio will lead the ITS project portfolio function, providing leadership, portfolio planning, governance, and project management to support business needs. This role will establish and monitor best practices and standard approaches, promoting the continuous improvement of project management-related processes throughout the organization. The Manager of IT Project Portfolio will report to the Director of Enterprise Solution Delivery and will supervise the project management team.

The Manager, IT Project Portfolio will be held accountable for the following responsibilities:

• Establish and maintain a Project Portfolio Management Center of Excellence to provide services and support across CPS, providing excellent customer service to internal and external clients
• Provide leadership and guidance to a strong project management team, ensuring that consistent, right-sized project management methodology (e.g., Waterfall vs Agile) is applied
• Develop new and/or continually improve upon existing ITS project management methodologies and approaches:
• Develop and monitor a flexible and consistent project management methodology, including creating and promoting the use of templates, tools, processes, and project health metrics to measure and ensure project success
• Develop a project prioritization, intake, and portfolio review approach by collaborating closely with business and technology partners to ensure transparency, consistent direction and development priorities
• Identify gaps and provide recommendations for improvement in current project methodology and overall project performance
• Provide training, project leadership, and consultation to the enterprise and to project leaders; foster a clear understanding of project methodology across the organization through offering learning opportunities and hands-on support to project managers and project support staff
• Provide high-level project management guidance and oversight:
• Participate in project-level assessments for the team; manage strategic projects according to the appropriate methodology when required
• Define project scope, processes, procedures and project management methodology and organization structure
• Provide project leadership, including guidance on work direction and feedback to stakeholders, project leads and teams
• Oversee, monitor and report progress, project status, and other deliverables on multiple, complex projects at each stage, relative to schedules, budgets and quality
• Assign project work, coordinate, and track work across teams in the organization to achieve project deliverables and goals
• Assist with the resolution of project issues that have been escalated for guidance
• Negotiate and resolve conflicting change requests and changing priorities across customers/projects to facilitate solutions to complex problems
• Build high-quality working relationships with executives, technology partners, customers, and all other relevant individuals and groups; effectively manage stakeholder and vendor relationships in accordance to CPS and ITS strategies and directives
• Other duties as assigned

In order to be successful and achieve the above responsibilities, the Manager, IT Project Portfolio 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 Institute’s Project Management Professional (PMP), Professional Scrum certifications, Scaled Agile Framework (SAFe) Lean-Agile, and/or IT Infrastructure Library (ITIL), preferred

Experience Required:

• Minimum of seven (7) years of relevant professional project management experience leading large and complex project portfolios, including the following, is required:
• Minimum of three (3) years of experience in a supervisory/management position responsible for leading teams of direct reports
• Experience implementing and using enterprise IT project management tools and systems to meet project, portfolio, and program management requirements (ex: Microsoft Project, Smartsheet, Clarizen, Jira, Azure DevOps, GanttPro, etc.)

Knowledge, Skills, and Abilities:

• Ability to build a CMMI-Level 5 IT Project & Portfolio Management Office supporting multi-year ERP Programs and annual ITS Projects
• Expert-level knowledge, understanding and capabilities in the following:
• Implementation of enterprise IT PMO tools and systems to meet project, portfolio, and program management requirements.
• Project management methodologies, practices, principles, tools, processes, and Software Development Lifecycle (SDLC)
• Planning, directing and implementing complex projects on time, within budget and with desired functionality
• Capable of success as a collaborative member of a team as well as working independently, proactively, and creatively toward a shared vision while maintaining alignment and overall direction;
• Effective prioritization and time management capabilities, including the ability to manage multiple projects simultaneously, driving them to completion and achieving success
• Strong written and verbal communication skills, including capabilities in conflict resolution, negotiation, and influence
• 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
• Knowledge of operations, budget/finance, management and organizational development
• Ability to build effective, collaborative relationships with a variety of stakeholders at all levels of the organization, including external partners, to ensure the IT project management team operates in the most effective manner possible to support schools, principals, and organizational success
• Ability to define problems, analyze data, and outline valid conclusions and action steps

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