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Security You Should Know · Monday · 16 min

Proving Readiness with TryHackMe

In this episode, Ashu Savani, co-founder of TryHackMe, explains how the company's Live Breach product puts teams inside fully-executed, realistic breach simulations built around the threat actors and tech stacks they face, building the reflexes and reporting security leaders need before a real incident hits. Joining him are Roland Toussaint, Senior Director of Incident Response and Security Engineering at ChenMed, and Heather Hinton, CISO at Sitecore. Want to know: How can a simulated environment realistically reflect a security team's actual tech stack and the threat actors they care about? Can TryHackMe's reporting help security leaders prove upskilling progress to auditors and cyber insurance carriers? How does TryHackMe help teams train for incidents caused by their own people, not just outside attackers? How granular can training get: can a team run a meaningful exercise in just 15 to 20 minutes? How are TryHackMe's custom exercises tiered and packaged across its plans? What's TryHackMe's track record getting cyber insurance carriers to accept its exercises as sufficient proof of readiness? Does TryHackMe offer anything built specifically around HIPAA for healthcare organizations? Why is crisis communication often more under-rehearsed than technical response, and how does TryHackMe help teams practice it? Check out the episode for the answers you need. Huge thanks to our sponsor, TryHackMe Live Breach challenges security teams to test their incident response against a rogue AI agent in a realistic, three-hour exercise. The campaign uses a compelling AI-driven attack scenario to create urgency, while highlighting the low-risk setup, actionable readiness insights and practical value of testing teams before a real incident occurs. Business applicants only, 18+. Applications open 7 October 2026 and close 18 October 2026 at 23:59 EST time. Six companies are selected by a TryHackMe panel from eligible applications, against published criteria; each receives one complimentary simulated Live Breach exercise. No purchase necessary. Full terms: http://tryhackme.com/legal/live-breach-giveaway-terms

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transcript

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show notes

In this episode, Ashu Savani, co-founder of TryHackMe, explains how the company's Live Breach product puts teams inside fully-executed, realistic breach simulations built around the threat actors and tech stacks they face, building the reflexes and reporting security leaders need before a real incident hits. Joining him are Roland Toussaint, Senior Director of Incident Response and Security Engineering at ChenMed, and Heather Hinton, CISO at Sitecore.

Want to know:

  • How can a simulated environment realistically reflect a security team's actual tech stack and the threat actors they care about?
  • Can TryHackMe's reporting help security leaders prove upskilling progress to auditors and cyber insurance carriers?
  • How does TryHackMe help teams train for incidents caused by their own people, not just outside attackers?
  • How granular can training get: can a team run a meaningful exercise in just 15 to 20 minutes?
  • How are TryHackMe's custom exercises tiered and packaged across its plans?
  • What's TryHackMe's track record getting cyber insurance carriers to accept its exercises as sufficient proof of readiness?
  • Does TryHackMe offer anything built specifically around HIPAA for healthcare organizations?
  • Why is crisis communication often more under-rehearsed than technical response, and how does TryHackMe help teams practice it?

Check out the episode for the answers you need.

Huge thanks to our sponsor, TryHackMe

Live Breach challenges security teams to test their incident response against a rogue AI agent in a realistic, three-hour exercise. The campaign uses a compelling AI-driven attack scenario to create urgency, while highlighting the low-risk setup, actionable readiness insights and practical value of testing teams before a real incident occurs. Business applicants only, 18+. Applications open 7 October 2026 and close 18 October 2026 at 23:59 EST time. Six companies are selected by a TryHackMe panel from eligible applications, against published criteria; each receives one complimentary simulated Live Breach exercise. No purchase necessary. Full terms: http://tryhackme.com/legal/live-breach-giveaway-terms
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