Rapid7 Cybersecurity Summit 2026

Customer Panel: What CISOs Would Do Differently If Starting Today

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If today’s CISOs could start over, what would they change first?

In this closing panel, experienced CISOs and security leaders reflect candidly on the lessons they’ve learned running security programs through rapid change, growing complexity, and escalating threats. Rather than revisiting tools or roadmaps, the conversation focuses on what actually matters in 2026 - where leaders would simplify, what they would stop doing immediately, and which decisions had the greatest impact on reducing risk and building resilience.

This session offers practical perspective for security leaders at any stage, grounding the summit’s themes in real experience and leaving attendees with clarity, confidence, and a sharper sense of where to focus next.

Presenters

Gregory Pickett

Gregory Pickett

Cybersecuirty Expert, Hellfire Security

Jonathan Chow

Jonathan Chow

Chief Information Security Officer, Genesys

Chris Hippensteel

Chris Hippensteel

Director of Information Technology, New Resources Consulting

Tony Arnold

Tony Arnold

CISO, TSB Bank Limited