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Executive Director, Technology and Learning Systems Job Details

Job ID: 5815196

Application Deadline: Posted until filled

Posted: Jul 02, 2026 7:00 AM (UTC)

Starting Date: Immediately

Job Description

Under the direction of the Chief Systems and Services Officer, the Executive Director of Technology and Learning Systems provides strategic leadership, operational oversight, and enterprise governance for the District's technology environment. This role is responsible for ensuring that 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. The Executive Director serves as the primary executive accountable for technology planning, technology investments, cybersecurity risk mitigation, and enterprise system integration.

This position maintains the confidentiality of all personnel and management matters; some duties involve access to confidential information concerning employer-employee relations and negotiations.

Representative Duties

Incumbents may perform any combination of the essential functions shown below. This position description is not intended to be an exhaustive list of all duties, knowledge, or abilities associated with this classification, but is intended to reflect the principal job elements accurately.

Essential Functions 1. 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 districtwide ecosystem.
• Establish alignment between Technology Services and Academics so that technology directly supports classroom instruction and student achievement.

2. 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.

3. 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.

4. 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 districtwide cybersecurity awareness and training programs to reduce human risk factors and strengthen organizational resilience.
• Establish and monitor key cybersecurity performance indicators and risk metrics.

5. Technology Service Delivery and Infrastructure

• Oversee districtwide 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.

6. Financial Stewardship and Lifecycle Planning

• Develop and manage the department's operating and capital budgets.
• Implement Total Cost of Ownership methodologies for technology investments.
• Align technology replacement cycles with fiscal planning and bond programs where applicable.
• Identify opportunities for cost savings through consolidation, standardization, and strategic sourcing.
• Implement technology portfolio management practices to evaluate system effectiveness, utilization, and return on investment.
• Lead efforts to consolidate, standardize, and sunset redundant or underutilized systems.

7. Integration with Facilities and District Operations

• Coordinate planning for technology infrastructure in modernization and construction projects.
• Support implementation of smart building systems, network backbone upgrades, and classroom technology modernization.
• Partner with Facilities, Enrollment, Finance, and Instructional divisions to ensure enterprise system effectiveness.
• Ensure technology infrastructure planning is fully integrated into capital projects, including modernization, new construction, and bond-funded initiatives.
• Align technology systems with smart building infrastructure, energy management systems, and campus safety systems.

8. Leadership and Organizational Development

• Lead and develop a high-performing technology leadership team.
• Supervise key leaders responsible for enterprise architecture, cybersecurity, infrastructure, applications, and technology service delivery.
• Promote a culture of accountability, innovation, and customer service.
• Develop succession-planning and workforce-capacity strategies.
• Lead change management strategies for major technology initiatives to ensure successful adoption and implementation.
• Ensure systems are designed and implemented with a focus on usability, accessibility, and the needs of diverse users.
• Partner with departments to align training, communication, and support structures for new system rollouts.
• Perform related duties as assigned.

Qualifications

The District determines whether a candidate is qualified based on fulfillment of prerequisites, relevant work experience, ability to perform the essential functions, reference checks, effective interpersonal and communication skills demonstrated by interview performance and/or writing samples, and achievement on performance-based assessments (if applicable) that demonstrate the candidate possesses the requisite knowledge, skills, and abilities.

Knowledge of

• Principles and practices of enterprise technology architecture, infrastructure, and system integration
• Cybersecurity frameworks, risk management, incident response, and disaster recovery and business continuity planning
• Instructional and digital learning systems, including learning management and assessment platforms
• State and federal laws and regulations governing student data privacy and technology security, including FERPA, COPPA, CIPA, and California student data privacy law
• Enterprise systems, including student information, human resources and payroll, and financial systems
• Cloud services, automation, artificial intelligence, and emerging technology trends
• Technology procurement, vendor management, and Total Cost of Ownership methodologies
• Public school district finance, budgeting, and bond and capital program planning
• Principles of strategic planning, enterprise governance, project and portfolio management, and change management
• Principles of supervision, leadership, and organizational development
• Correct and persuasive English usage, grammar spelling vocabulary, and punctuation
• District policies, applicable sections of the State Education Code, and other laws and regulations

Abilities To

• Develop and execute a multi-year enterprise technology strategy aligned with District goals
• Lead and develop a high-performing technology leadership team and supervise senior managers
• Establish and enforce enterprise standards for architecture, security, and interoperability
• Provide executive oversight of cybersecurity strategy, risk mitigation, and incident response
• Develop and manage operating and capital budgets and apply Total Cost of Ownership methods
• Analyze complex problems, evaluate alternatives, and make sound recommendations
• Communicate effectively orally and in writing, including presentations to the Board and executive leadership
• Build effective partnerships across academic, business, facilities, and operational divisions
• Manage vendors and complex, multi-million-dollar contracts
• Lead change management and the successful adoption of major technology initiatives
• Ensure consistent and equitable access to technology across all schools
• Establish and maintain effective working relationships and be sensitive and responsive to diverse cultural and ethnic groups
• Exercise sound, independent judgment on high-risk and high-investment matters
• Use a computer and enterprise technology systems

Prerequisites

• Bachelor's degree in Information Technology, Computer Science, Public Administration, or a related field; Master's degree preferred
• Minimum of seven (7) to ten (10) years of progressively responsible leadership experience managing technology environments
• Experience in cybersecurity governance, enterprise systems management, or large-scale technology operations
• Experience managing multi-million-dollar operating and capital budgets and complex vendor relationships
• Experience leading enterprise technology initiatives in large public or private organizations; experience in a K-12 or public-sector environment is highly desirable
• Valid California Driver's License, if applicable

Pre-Employment Process

Employment eligibility will include fingerprints, tuberculosis clearance, and/or other employment clearance.

Working Conditions Environment

Office, data center, and diverse school site environments; driving a vehicle to conduct work; fast-paced work with frequent deadlines and constant interruptions; occasional evening and weekend work and on-call response to technology and security incidents.

Physical Requirements

Consistent mental alertness; sitting or standing for extended periods of time; lifting, carrying, pushing, and pulling objects up to 30 pounds, occasionally 30 or more pounds; bending and twisting at the waist, reaching overhead, above the shoulders, and horizontally; dexterity of both hands and fingers while performing duties; seeing to read, write, and use the computer; hearing and speaking to exchange information, in person or on the telephone, and to make presentations.

Non-Discrimination Policy

The Oakland Unified School District does not discriminate in any program, activity, or in employment on the basis of actual or perceived race, religion, color, national origin, ancestry, immigration status, age, marital status, pregnancy, physical or mental disability, medical condition, genetic information, veteran status, gender, gender identity, gender expression, sex, or sexual orientation.

Position Type: Full-Time

Job Requirements

• Citizenship, residency or work visa required