Executive Director, Technology and Learning Systems
Listed on 2026-07-08
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IT/Tech
Cybersecurity, IT Project Manager, IT Consultant
Executive Director, Technology and Learning Systems
Oakland Unified School District Technology Services - Oakland, California
Job DetailsJob : 5815196
Final date to receive applications: Posted until filled
Posted: Jul 02, 2026 7:00 AM (UTC)
Starting Date: Immediately
Job DescriptionThe Executive Director of Technology and Learning Systems, under the direction of the Chief Systems and Services Officer, provides strategic leadership, operational oversight, and enterprise governance for the District's technology environment. This role is responsible for ensuring technology systems are secure, reliable, fiscally sustainable, and aligned with instructional priorities and operational needs. The Executive Director modernizes and coordinates the District's technology infrastructure, digital systems, cybersecurity strategy, and service delivery model to support student learning and district performance, while serving as the primary executive accountable for technology planning, technology investments, cybersecurity risk mitigation, and enterprise system integration.
ESSENTIALFUNCTIONS
Strategic Leadership and Technology Vision
- Develop and implement a multi-year enterprise technology strategy aligned with District goals.
- Serve as a key advisor to executive leadership on technology modernization, cybersecurity risk, and digital transformation.
- Present to the Board and formal governance structures the role that technology investments and initiatives play in operational and learning systems.
- Lead the development of technology roadmaps that support instructional innovation, operational efficiency, and data-driven decision-making.
- Monitor emerging trends, including artificial intelligence, cloud services, automation, and smart infrastructure.
- Define and lead a comprehensive digital transformation strategy that integrates instructional technology, enterprise systems, and data platforms into a cohesive district wide ecosystem.
- Establish alignment between Technology Services and Academics so that technology directly supports classroom instruction and student achievement.
Instructional Technology and Digital Learning Systems
- Provide executive leadership for the District's digital learning ecosystem, including learning management systems, assessment platforms, and instructional applications.
- Establish governance processes for the evaluation, selection, implementation, and sunset of instructional technology tools.
- Partner with academic leadership to ensure technology investments support curriculum, instruction, and student engagement.
- Ensure alignment between digital tools, teacher professional learning, and classroom implementation.
- Monitor and evaluate the impact of instructional technology on student outcomes and instructional practice.
Enterprise Technology Governance
- Establish standards for technology architecture, cybersecurity, and system integration across the District.
- Ensure coordination between instructional systems, business systems, and infrastructure platforms.
- Oversee technology procurement strategy and vendor management practices to optimize performance and cost.
- Lead cross-departmental planning for enterprise initiatives involving student information systems, human resources and payroll systems, financial systems, facilities technology, and digital learning platforms.
- Ensure compliance with state and federal regulations related to student data privacy and technology security.
- Establish and enforce enterprise standards for system interoperability, data integration, and platform consolidation.
- Lead governance structures that prioritize technology investments based on educational impact, operational need, and return on investment.
Cybersecurity and Risk Management
- Provide executive oversight of the District's cybersecurity strategy, incident response planning, and risk mitigation efforts.
- Ensure implementation of cybersecurity frameworks, security awareness programs, and monitoring practices.
- Coordinate disaster recovery and business continuity planning for technology systems.
- Evaluate cyber risk exposure and provide recommendations to executive leadership and the Board.
- Lead district wide cybersecurity awareness and training programs to reduce human risk factors and strengthen organizational resilience.
- Establish and monitor key cybersecurity performance indicators and risk metrics.
Technology Service Delivery and Infrastructure
- Oversee district wide technology operations, including network reliability, device lifecycle management, help desk services, and school-site technology support.
- Ensure consistent and equitable access to technology resources across all schools.
- Monitor service performance metrics and implement continuous improvement practices.
- Support long-term infrastructure planning, including network modernization, cloud migration, and systems replacement cycles.
Financial Stewardship and Lifecycle Planning
- Develop and manage the department's operating and capital budgets.
- Implement Total Cost of Ownership methodologies for technology…
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