Rob Cryan

Rob Cryan is leading the technology strategy behind one of the nation’s largest online learning providers as chief technology officer for Florida Virtual School (FLVS) and FlexPoint, the national arm of FLVS that serves schools and districts nationwide. In his role, Cryan helps shape and advance the organization’s technology vision, driving innovation in learning platforms, AI-driven services,  and digital tools that support student success and educational excellence.

As chief technology officer, Cryan oversees Learning Systems Engineering, Information Technology, Cybersecurity, and Agentic Services. He is responsible for the organization's overall technology direction — the multitenant SaaS learning platforms his engineering teams build to power FLVS and FlexPoint products, the enterprise IT systems and infrastructure that keep operations running, the cybersecurity practices that protect the organization and its data, and the data engineering, analytics, and agentic AI infrastructure that turn information into insight and action — all enabling scalable, secure, and innovative learning experiences for students, educators, and education partners.

Cryan brings more than 30 years of experience in technology leadership, cybersecurity, business operations, and enterprise services. Throughout his career, he has built a reputation for leveraging technology to solve complex challenges, drive operational excellence, and support organizational growth in rapidly evolving environments.

Cryan has extensive expertise in information security, risk management, and technology strategy. Prior to joining FLVS, he held senior leadership roles spanning business and financial operations, cybersecurity, and technology, where he guided organizations through technological transformation and strengthened their security posture.

Before entering the private sector, Cryan served in the United States Marine Corps, specializing in electronic countermeasures. His military experience provided an early foundation in technology, security, and mission-focused leadership that continues to influence his approach today.

With a deep background in technology innovation and cybersecurity, Cryan plays a critical role in ensuring FLVS remains at the forefront of digital learning, delivering secure, AI-enabled, and data-driven educational solutions for students and partners in Florida and across the nation.

Education

• Master of Science in Information Systems and Technology Management, Information Assurance & Security, Capella University in Minneapolis, Minnesota
• Bachelor of Science in Business Administration Management, University of Maine