Rob Cryan

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

As chief technology officer, Cryan oversees Learning Systems Engineering, Information Technology, Data Services, Cybersecurity, and Accountability. He is responsible for ensuring that the organization's technology infrastructure, data systems, and cybersecurity practices support the organization's mission while enabling scalable, secure, and innovative learning experiences for students, educators, and education partners nationwide. He also leads efforts to develop and enhance multitenant software-as-a-service (SaaS) learning systems that power the products and services offered through FlexPoint and FLVS.

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.

A Certified Information Systems Security Professional (CISSP) since 2005, 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 the organization remains at the forefront of digital learning, delivering secure, data-driven, and reliable 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