Show Notes
A busy cybersecurity program is not necessarily a well-run one. The difference is whether the work protects the business, supports growth, and gives leaders confidence that the company can respond and recover when something goes wrong.
In this episode of The Blind Spot, Jason Lee sits down with Brian Herr, founder of Startup Starting Blocks Inc. and a security and industry advisor, to discuss what it takes to build and manage a cyber program in 2026. They cover the five business priorities that should shape security decisions, why program design should start with critical business processes instead of tools, what boards actually need to see, how to align cyber insurance with real exposure, and how tool consolidation can improve coverage while lowering spend. They also discuss how AI is changing security governance, team structure, career paths, and the way leaders manage burnout.
About the host Jason Lee is Managing Director at Z Cyber. For more than 20 years he has worked the part most people skip past: what happens after the risk is visible, across infrastructure, AI, and GRC.
About the guest Brian Herr is the founder of Startup Starting Blocks Inc. and a security and industry advisor. He advises companies and boards on how to connect cybersecurity strategy, operations, spending, and recovery to the needs of the business.
About Z Cyber Z Cyber is the security team that builds, runs, and improves your program through an Executive Security Advisor and Glance, its AI-native GRC platform.
Links Z Cyber: https://www.ztekcyber.com The Blind Spot: https://www.ztekcyber.com/resources/the-blind-spot Apply to be a guest: https://www.ztekcyber.com/resources/the-blind-spot/apply Get started with Z Cyber: https://www.ztekcyber.com/get-started
More from The Blind Spot
When the CTO, the CIO, and the CISO disagree about AI in the same room, the person who wins is rarely the person who is right. It is the one who can tie the decision to a business outcome, and who has earned enough trust that a no actually means no.
Most organizations believe they know where their sensitive data lives. That confidence often disappears as soon as they scan the environment. Files have been copied into personal folders, cloud storage, SaaS platforms, and systems that were never included in the original security plan. AI can now reach much of that data faster than teams can classify or govern it.
A point-in-time security assessment can be out of date the moment the report arrives. When new vulnerabilities can move from detection to exploitation in hours, the harder problem is no longer finding more. It is knowing which ones matter and fixing them fast enough.
Security leaders often talk about risk. CFOs hear cost, trade-offs, timing, probability, and whether the decision can be defended to the CEO or the board.
Boards and CISOs are often on two different planes. In the first episode of The Blind Spot, Jason Lee sits down with Antonio Bovoso, cybersecurity executive and author of The Boardroom CISO, on why security and the board talk past each other and how to close the gap. They get into reframing risk as enablement, tying cyber to how the business actually makes money, cutting vanity metrics and the museum-quality deck, and where cyber liability really lands.