The Human Stories Behind the Cyber Crisis
Season 1
Inside the Attack That Tested Every Ounce of Resilience
Even the best defenses can be tested. In this episode of Wake Up, the podcast by Veeam, Caroline Wong and Michael Irwin unpack how one organization faced a nation-state cyberattack and what it revealed about leadership under pressure. Through real-world lessons in containment, communication, and recovery, they explore how data resilience is not only a technical goal but a culture of readiness that defines confident organizations.
The Cost of Being Right: What Happens When the Warnings Come True
When a cyber incident strikes, the technical response is only half the story. In this episode of Wake Up, host Caroline Wong speaks with Vanessa Pegueros, a seasoned CISO who reveals what it feels like to lead through chaos, exhaustion, and organizational shock. Together they unpack the emotional toll of incident response, the importance of calm leadership, and why resilience begins with people as much as with technology.
The CISO Who Carried Too Much
When a ransomware attack crippled a company he once protected, fractional CISO Tim Silverline felt the failure as if it were his own. He’d built their defenses, trained their teams, and left them with a plan — but when they stopped following it, everything unraveled. This is the story of responsibility without control, of guilt without blame — and what happens when the person who guards resilience carries too much of it alone.
The CISO Carrying a Nation
What happens when one security leader is responsible for protecting the nation’s largest healthcare payer — and the stakes include 130 million Americans? In this episode of Wake Up, global data resilience expert Caroline Wong sits down with Robert Wood, former CISO of the Centers for Medicare & Medicaid Services (CMS), to talk about leading security at scale, managing complex contractor networks, and balancing human pressure with national responsibility. From SolarWinds to MOVEit, Robert shares what it’s really like inside the federal cybersecurity war room — the politics, the sleepless nights, and the lessons that keep leaders grounded. Cybersecurity is complex. Accountability is what keeps it clear.
Inside the Mind of the Modern Hacker
They look nothing like the villains you imagine. From scattered collectives of teenagers to AI-powered deepfakes, the battlefield has shifted — and Ray Heffer has watched it happen in real time. He reveals how the next generation of threat actors are turning human trust into their most powerful weapon.
Season 1 Featured Host
Caroline Wong
Cybersecurity Director, Author & Speaker
Caroline Wong is a cybersecurity executive, author, and educator with two decades of experience leading global security, risk, and compliance programs. She currently serves as Cybersecurity Director at Teradata and is the author of Security Metrics: A Beginner’s Guide (McGraw-Hill), a book inducted into the Cybersecurity Canon Hall of Fame. Caroline is also writing The AI Cybersecurity Handbook (Wiley, 2026), exploring the intersection of artificial intelligence and digital defense.
Caroline Wong
Cybersecurity Director, Author & Speaker
Caroline Wong is a cybersecurity executive, author, and educator with two decades of experience leading global security, risk, and compliance programs. She currently serves as Cybersecurity Director at Teradata and is the author of Security Metrics: A Beginner’s Guide (McGraw-Hill), a book inducted into the Cybersecurity Canon Hall of Fame. Caroline is also writing The AI Cybersecurity Handbook (Wiley, 2026), exploring the intersection of artificial intelligence and digital defense.
Season 1 Featured Guests
Michael Irwin
CISO and VP, Technology Operations, Odyssey Logistics
Michael Irwin is the Chief Information Security Officer (CISO) and Vice President of Technology Operations at Odyssey Logistics, where he leads global cybersecurity and risk, IT infrastructure, cloud, and technology operations. Since joining Odyssey in 2022, Michael has established the company’s global cybersecurity program, developed a unified shared services organization, and led a comprehensive IT transformation initiative.
Vanessa Pegueros
Corporate Board Member, Cybersecurity Leader, and Former CISO
Vanessa Pegueros is an accomplished technology executive with over 30 years of experience. Currently she serves as a Corporate Board Director of the public company Liveperson (NASDAQ: LPSN), Boeing Employee Credit Union, and Prisidio. Formerly she was on the board of Carbon Black (NASDAQ: CBLK) and was part of the transaction to sell Carbon Black to VMware.
Tim Silverline
VP of Security at RocketLawyer and former Fractional CISO
Tim Silverline has been the Vice President of Security at RocketLawyer since September 2024, managing the Security, IT and Cloud teams. He focuses daily on maturing RocketLawyer's security program to defend against threats and protect customer data. Working in the cybersecurity space for more than twenty years for companies of all sizes, Tim has architected and built out platforms to deliver customer services securely for many organizations.
Robert Wood
CEO, Sidekick Security (formerly CISO at Centers for Medicare and Medicaid Services)
Robert Wood has built and led security programs across Silicon Valley startups to one of the largest U.S. Federal agencies. Robert led cybersecurity for the Centers for Medicare and Medicaid Services throughout the COVID-19 response. Robert bridges the gap as a leader between bold technical vision and the people and culture needed to drive true value in cybersecurity.
Ray Heffer
Field CISO at Veeam
As a Field CISO at Veeam, Ray works closely with clients in the wake of cyberattacks, helping them respond to threats and rethink how they approach risk. Known for challenging the idea that "humans are the weakest link," Ray brings a unique blend of technical insight and behavioral psychology — with a focus on the moments between alerts, not just the alerts themselves.
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