VP of Technology & AI Infrastructure

About the Opportunity

A national workforce development organization dedicated to connecting skilled, work-authorized professionals to career-aligned employment across the United States is seeking a VP of Technology & AI Infrastructure. The organization focuses on creating economic opportunity, scaling programmatic impact, and leveraging modern technology and artificial intelligence to drive operational efficiency and positive participant outcomes.

Role Overview

The VP of Technology & AI Infrastructure is responsible for defining and executing the organization’s technology strategy and infrastructure across internal operations and externally facing digital products. Reporting to the President and working closely with the CEO and executive leadership, this leader guides the organization toward an AI- and product-first model while upholding operational excellence, security, reliability, and scalable delivery practices. This role operates in a full-time, remote capacity within the United States.

Key Responsibilities

• Own the overarching technology strategy across staff infrastructure and external user- and partner-facing products, ensuring systems are secure, scalable, cost-effective, and mission-aligned.
• Build and maintain a multi-year technology roadmap encompassing staff infrastructure, IT operations, data systems and reporting, platform evolution, core digital products, and system integrations.
• Translate organizational strategy into sequenced roadmaps with defined timelines, dependencies, resource requirements, and metrics.
• Provide executive leadership with clear tradeoff analyses and recommendations on priorities based on organizational capacity and impact.
• Support Agile ceremonies, including sprint planning and release planning.
• Partner with product leadership to guide technical architecture, build-versus-buy evaluations, platform selection, integration strategy, and delivery for participant and partner platforms.
• Establish technical standards and governance for responsible AI adoption in collaboration with cross-functional committees, covering data privacy, security controls, vendor risk management, quality assurance, bias mitigation, and human oversight.
• Build the technical foundation for AI readiness, focusing on data quality, system integrations, and scalable infrastructure for feature deployment and experimentation.
• Oversee internal IT operations and service delivery, including help desk support, hardware lifecycle management, access controls, onboarding, offboarding, and technical troubleshooting.
• Define IT service standards, manage vendor relationships and managed service provider contracts, and lead staff training initiatives to maximize adoption of organizational infrastructure and AI tools.
• Oversee the customer relationship management (CRM) platform and associated systems as the operational backbone for programs, development, and reporting.
• Direct enterprise data strategy in collaboration with research and evaluation leadership to maintain reliable governance, dashboards, and reporting for program improvement, funding requirements, and executive decision-making.
• Implement a consistent project management framework across technology initiatives to maintain accountability, predictability, and cross-functional transparency.
• Lead cybersecurity strategy, data protection controls, and operational risk management, maintaining a risk register and presenting mitigations to executive leadership and the Board.

Required Qualifications

• 10+ years of technology leadership experience spanning IT operations, systems leadership, and product/engineering delivery.
• Proven experience building or leading technology strategy across both internal infrastructure and externally facing digital products or platforms, including demonstrated experience with artificial intelligence.
• Strong program and project delivery discipline with the ability to manage competing priorities in a resource-constrained environment.
• Experience with AI implementation, data governance, and enterprise systems.
• Demonstrated experience partnering with product leaders on strategy, roadmaps, prioritization, and technical execution.
• Strong executive communication skills with the ability to translate complex technical topics into actionable decisions for leadership.
• Demonstrated commitment to the organization’s workforce development mission.

Preferred Qualifications

• Experience with Sales…