Why Cybersecurity Is Becoming Every Company’s Biggest Risk
From Legends N Leaders by Ben Weiss
May 25, 2026 · 22 min
About this episode
The episode discusses the growing importance of cybersecurity and AI in business, featuring insights from Roger Lewis on managed IT services and leadership during technological change.
Every company is becoming a technology company. But most businesses still aren’t prepared for the cybersecurity, AI, and infrastructure challenges that come with it. In this episode of LegendsNLeaders, we sit down with Roger Lewis, CEO of CMIT Solutions, to discuss scaling a national technology brand, the future of managed IT services, and how AI is changing business operations. Since taking over CMIT, Roger has helped grow the company from $68M to $150M in revenue while building a service-driven organization designed to bring enterprise-level IT and cybersecurity support to small and mid-sized businesses across North America. Before CMIT, Roger worked at IBM supporting NASA and the Space Shuttle program — experiences that shaped his philosophy around scalable systems, operational discipline, and mission-critical execution. We discuss: The future of AI and cybersecurity for businesses Why SMBs are increasingly targeted by cyber threats How managed IT services are evolvingBuilding a franchise-based technology company at scale Creating a culture centered around service and trust What leadership looks like during rapid technological change This episode is a deep dive into…
People in this episode
Host: Ben Weiss
Guest: Roger Lewis
Topics covered
- cybersecurity
- AI
- managed IT services
- entrepreneurship
- leadership
- technology
Keywords
- cybersecurity
- AI
- managed IT services
- entrepreneurship
- leadership
- technology
- small and mid-sized businesses
- service-driven organization
- innovation
Mentioned in this episode
Organizations: CMIT Solutions, IBM, NASA, Space Shuttle program
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