IT Program Manager - 5 Year Limited Term

APPLICATION DEADLINE: Sunday, August 23, 2026 (1st cutoff Sunday, August 9, 2026)

The IT Program Manager is a 5-year limited term position. It is responsible for managing the IT Project Management Office for the San Mateo County Transit District (SamTrans), the Peninsula Corridor Joint Powers Board (Caltrain), and the San Mateo County Transportation Authority (TA).

Under general direction, plans, organizes, manages, and oversees the Division of Innovation & Technology’s enterprise information technology program and project portfolio; establishes and administers portfolio governance, project intake, prioritization, resource planning, budget tracking, vendor coordination, risk management, and performance reporting; leads complex, cross-functional technology initiatives supporting transit operations, administrative business functions, customer-facing services, cybersecurity, infrastructure modernization, and enterprise applications; and performs related duties as assigned. 

This position will be highly technical in nature with hands on expertise in running complex enterprise IT projects.

The following are representative of the functions and duties performed. They are not intended to be an exhaustive list.

Portfolio Strategy and Governance

• Develops, implements, and maintains an enterprise IT project portfolio management framework aligned with agency strategic goals, service delivery priorities, regulatory obligations, and budget constraints.
• Leads project intake, business case review, prioritization, sequencing, and portfolio planning for technology initiatives.
• Establishes and facilitates governance processes for evaluating scope, risk, funding, resource capacity, operational impact, and expected business value.
• Recommends portfolio tradeoffs and prioritization decisions to executive leadership based on cost, urgency, risk, compliance, and service impact.
• Maintains portfolio roadmaps for enterprise applications, infrastructure, cloud, cybersecurity, data, communications, and transit technology initiatives.

Program and Project Oversight

• Oversees and manages multiple large, complex, and interdependent IT projects and programs from initiation through implementation and transition to operations.
• Ensures projects are appropriately planned with defined scope, schedule, budget, milestones, dependencies, risks, staffing, procurement actions, and success metrics.
• Monitors portfolio health and project performance using dashboards, status reports, KPI tracking, and executive briefings.
• Identifies delivery risks, escalation points, resource conflicts, and change impacts; develops mitigation and recovery strategies.
• Promotes consistent use of project management standards, templates, controls, and documentation practices.

Business and Stakeholder Alignment

• Partners with business units, transit operations, maintenance, finance, procurement, HR, customer service, safety, and executive leadership to define project needs and expected outcomes.
• Translates operational and business priorities into executable technology roadmaps and implementation plans.
• Facilitates stakeholder meetings, steering committees, workshops, and executive decision sessions.
• Supports organizational change management, communication planning, training coordination, and adoption readiness for new technologies and processes.

Budget, Procurement, and Vendor Management

• Assists in development and administration of the IT capital and operating project portfolio budget.
• Tracks project expenditures, encumbrances, forecasts, and funding utilization.
• Coordinates procurement activities related to technology projects, including requirements development, scopes of work, RFP/RFQ support, proposal evaluation, contract administration support, and vendor onboarding.
• Oversees vendor, consultant, and systems integrator performance to ensure compliance with contractual obligations, schedules, deliverables, and service levels.
• Supports audit responses, funding documentation, and executive reporting related to projects and contracts.

Technology and Operational Coordination

• Coordinates initiatives affecting enterprise applications, servers, storage, networks, cloud services, cybersecurity controls, identity and access management, business continuity, and end-user platforms.
• Supports implementation of systems relevant to transit and public-sector operations, which may include ERP, HRIS, asset management, fare systems, dispatch/CAD-AVL, customer information systems, document management, data integration, and reporting platforms.
• Ensures proper transition from project delivery into production support, operations, maintenance, and service management.
• Works with technical teams to identify architecture, integration, security, support, and lifecycle implications of proposed projects.

Compliance, Risk, and Continuous Improvement

• Promotes compliance with applicable agency policies, information security standards, privacy requirements, records management practices, accessibility expectations, and public procurement requirements.
• Supports disaster recovery, business continuity, and operational resilience planning as related to technology initiatives.
• Develops and refines PMO, portfolio, and governance practices to improve delivery consistency, transparency, and accountability.
• Prepares reports, presentations, memoranda, and recommendations for executive staff, leadership committees, and, as assigned, governing board materials.

Sufficient experience, training and/or education to demonstrate the knowledge and ability to successfully perform the essential functions of the position. In lieu of a degree, work-related experience that demonstrates the skills and experience necessary to perform this role will be accepted. Development of the required knowledge and abilities is typically obtained through but not limited to: 

• Bachelor’s degree from an accredited college or university in information systems, computer science, public administration, engineering, or a closely related field.
• Five (5) years of full-time progressively responsible experience in information technology project or program management, business systems delivery, enterprise systems implementation, infrastructure modernization, or related IT work, including at least three (3) years of responsibility for managing complex cross-functional programs, project portfolios, PMO functions, or enterprise technology initiatives.

Preferred Qualifications:

• Ten (10) years of experience working within PMO functions.
• Experience overseeing both business application and infrastructure projects
• Experience with ERP, cloud migration, cybersecurity initiatives, enterprise integrations, data/reporting programs, or operational technology implementations
• Experience supporting formal procurement and vendor contract oversight
• Able to possess a valid California Class C driver’s license and a satisfactory driving record. 
• PMP, PgMP, PMI-ACP, ITIL, Scrum, or related certification is desirable

Knowledge of

• Principles and practices of project, program, and portfolio management
• PMO governance models, project intake, prioritization, resource planning, and benefits realization
• Public-sector budgeting, capital planning, procurement, contracting, and vendor management
• Information technology infrastructure, enterprise applications, systems integration, cloud services, cybersecurity, and service delivery
• SDLC methodologies including Agile, hybrid, and waterfall project delivery approaches
• Risk management, issue escalation, quality assurance, and change control practices
• Organizational change management and business process improvement principles
• Data analysis, reporting tools, dashboard development, and executive-level communication techniques
• Public agency operating environments, including cross-functional stakeholder coordination and accountability requirements
• Transit technology environments and operational dependencies, including customer-facing, operational, and administrative systems
• Applicable safety, security, documentation, and records retention practices relevant to government operations

Ability to

• Lead and coordinate a complex enterprise IT project portfolio with competing priorities and constrained resources
• Analyze business needs and translate them into strategic programs, roadmaps, and delivery plans
• Manage multiple large-scale projects simultaneously while maintaining visibility into scope, schedule, budget, risk, and dependencies
• Establish governance disciplines and gain stakeholder alignment on priorities and sequencing
• Communicate effectively with technical teams, executives, business managers, vendors, and external partners
• Prepare clear, concise, and accurate reports, recommendations, presentations, and project documentation
• Interpret contracts, statements of work, procurement documents, and vendor deliverables
• Build effective cross-functional working relationships in a public-sector environment
• Exercise sound judgment, diplomacy, and problem-solving in politically and operationally sensitive situations
• Supervise, coach, and evaluate staff where assigned
• Maintain focus on customer service, reliability, compliance, and operational continuity
• Create Executive Management Reports, Dashboards and Debriefs

Examples of Agency-Relevant Projects
For a transit agency, this role may oversee programs such as:

• Enterprise application modernization
• ERP or HRIS implementation
• Network and infrastructure refresh
• Cloud migration and identity modernization
• Cybersecurity risk reduction initiatives
• Data integration and reporting platforms
• Asset management or maintenance systems
• Fare collection and customer information systems
• Dispatch, scheduling, or operational technology upgrades
• Business continuity and disaster recovery improvements