What separates a CISO who survives from one who shapes the boardroom? In this episode, Steve Moore sits down with Walt Powell, Lead Field CISO at CDW and author of The CISO 3.0, to unpack the modern CISO playbook—why technical credentials alone no longer cut it, how to build personal eminence, and why most security leaders are still treated as second-class C-suite citizens.

Walt traces his path from teaching networking before stateful firewalls existed, to writing CISSP exam questions for ISC2, to running CDW's Global Security Strategy Office. He explains what a field CISO does, why the role is harder than ex-CISOs realize, and how one bad meeting can tarnish a brand built over decades.

He and Steve break down the four pillars Walt uses to measure his team—embedded advisory, eminence building, sales enablement, and voice of the customer—and how a karate-style “belt system” maps each consultant's competency. Walt explains why the same skills matrix from The CISO 3.0 works for any CISO trying to spot their own gaps.

Walt argues a CISO who is not liked cannot succeed: you are the talent magnet, the culture builder, and the person proving in every board meeting that you belong in the seat. He shares the questions every candidate should ask before accepting the role—from D&O coverage to 10-K disclosure access—and why the 30-60-90 plan should be written before the second interview, not after the offer.

The conversation closes with what Walt calls “strategic debt”—the identity and data governance work organizations skipped a decade ago that is now blocking AI adoption. Walt shares lessons from running OpenClaw on a Mac mini, why non-human identity tops every 2026 CISO worry list, and how Deep Research is reshaping senior architects.

Key Topics

• The modern field CISO role and the four pillars of impact

• Why CISOs are still treated as second-class C-suite citizens

• Building personal eminence through books, speaking, and writing

• The CISO 3.0 skills matrix and self-assessment spider wheel

• Two paths to the CISO seat: technical vs. MBA, and the gaps each leaves

• Why likability is not optional for a successful CISO

• Board readiness and proving you belong in the seat

• Interview questions every CISO candidate must ask

• Strategic debt: identity and data governance blocking AI adoption

• OpenClaw, non-human identity, and the future of senior architects

Guest Bio:

Walt Powell is the Lead Field CISO at CDW and a founding member of CDW's Global Security Strategy Office, where he leads a team of former CISOs advising security leaders in the field. A longtime executive coach and ISC2 exam development committee member, Walt is the author of The CISO 3.0: A Guide to Next-Generation Cybersecurity Leadership and Quantum Ready, his book on post-quantum cryptography.

Connect with Walt on LinkedIn or at ciso30.com.

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What happens when an AI agent inside your company starts behaving like an insider threat? In part two, Steve Moore picks the thread back up with former FBI operative Eric O'Neill to explore how agentic AI is rewriting cybersecurity, the legal traps that follow a breach, and why the modern CISO must think like a spy hunter.

Eric opens with a sobering reality: ransomware victims who decline to pay are re-attacked at staggering rates. He explains why criminals treat cybercrime as a business, invest weeks in reconnaissance—mapping SharePoint, harvesting file trees, and studying access patterns—and why a botched recovery hands them the same door twice.

The conversation turns to the new insider threat hiding in plain sight: rogue AI agents. Eric shares a real case in which one executive's casual query exposed the next round of layoffs and triggered coordinated lawsuits. They unpack how agents inherit excessive access, how attackers hijack them once inside, and why organizations are now building insider-threat programs to monitor AI behavior.

Eric argues AI is an accelerant on every unresolved problem—weak identity management, entitlement drift, missing asset inventories, and absent data classification. They debate whether IT and security should be unified under the CISO, why the CISO needs a direct line to the board, and the legal landmines that follow a breach, from cyber insurance to the “reasonable steps” standard.

The episode closes with Eric's advice for any new CISO: put “spy hunter” on your resume. Counterintelligence, not perimeter defense, is the discipline that wins today. Tune in for part two of a story-driven conversation on why preparation, mindset, and threat hunting beat any single technology.

Key Topics

• Why ransomware victims who decline to pay get re-attacked

• How attackers map SharePoint, file trees, and access patterns

• The new insider threat: rogue and hijacked AI agents

• A real case of an AI agent exposing an HR layoff list

• Shadow IT and the cost of banning AI outright

• Permission structures and second-level reviews for agent actions

• Why AI exposes gaps in identity, asset, and data classification

• Unifying IT and security under the CISO

• Why the CISO needs a direct line to the board

• Legal traps: cyber insurance, reasonable steps, and missed alerts

• The CISO as counterintelligence officer and spy hunter

Guest Bio

Eric O'Neill is a former FBI counterintelligence operative, attorney, and bestselling author who helped bring down Robert Hanssen—the most damaging spy in FBI history. He is the founder of NeXasure AI and co-founder of The Georgetown Group, and his undercover work was dramatized in the film Breach. Eric is the author of Gray Day and Spies, Lies, and Cybercrime.

Connect with Eric on LinkedIn or at ericoneill.net.

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What does it feel like to stand in the smoking ruin of a ransomware attack? In this episode, Steve Moore is joined by former FBI undercover operative Eric O'Neill—the man who helped capture Robert Hanssen—to explain why modern cybercrime is just traditional espionage repackaged, and why the dark web has quietly become the world's third-largest economy.

Eric traces his path from the FBI's counterintelligence trenches to founding NeXasure AI and writing cybersecurity books that read like spy thrillers. He and Steve unpack the staggering scale of cybercrime, which Eric predicts could reach $20 trillion in global GDP within years—a marketplace selling everything from ransomware kits to stolen credentials.

They dismantle the “it won't happen to me” mindset that still lingers in boardrooms. Eric describes how attackers use AI agents to scan for vulnerable systems, walks through how Scattered Spider socially engineered MGM in a ten-minute phone call, and explains why disabled MFA remains the leading point of failure for small and mid-size businesses.

Eric then unpacks the painful calculus of paying a ransom. He explains why the FBI says never pay, when OFAC sanctions make payment a federal crime, and why—even after paying—an organization must still do the same forensic, legal, and architectural work. Steve and Eric also detail how attackers resell access and treat victims as repeat customers.

The episode closes with a candid look at recovery. Eric and Steve explore why most companies fail at restoration, why rolling back to “before the attack” leaves the original flaw wide open, and why preparation always beats panic. Tune in for a part-one masterclass for any leader who thinks their organization is too small to be a target.

Key Topics

• How traditional espionage evolved into modern cybercrime

• The dark web as the world's third-largest economy

• Why every organization is a target, regardless of size

• The MGM ransomware attack and Scattered Spider's playbook

• Disabled MFA as the leading cause of SMB compromise

• Vulnerability assessments versus fire-time remediation costs

• The pay-versus-don't-pay ransomware calculus

• OFAC sanctions and the legal risks of paying

• Why restoring backups is not the same as recovery

• The how, where, why, what, and when of breach forensics

Guest Bio

Eric O'Neill is a former FBI counterintelligence operative, attorney, and bestselling author who helped bring down Robert Hanssen—the most damaging spy in FBI history. He is the founder of NeXasure AI and co-founder of The Georgetown Group, and his undercover work was dramatized in the film Breach. Eric is the author of Gray Day and Spies, Lies, and Cybercrime.

Connect with Eric on LinkedIn or at ericoneill.net.

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Cybersecurity debates tend to center on tools, frameworks, and threats. But Rob Knoblauch has built a 25-year career in global security leadership by focusing on the soft skills that determine whether a CISO survives, thrives, or burns out. In this episode of The New CISO, Rob joins Steve Moore to trace the through-line from running a multi-node BBS as a kid to serving as Deputy CISO of one of the world’s largest banks — and the career lessons he’s carried through every chapter.

Rob’s path wasn’t engineered. It began with a VIC-20, a love of video games, and a side passion for DJing that eventually clinched his first big bank interview. Running a BBS taught him identity management, patching, and infrastructure long before those were industry terms, and responding to the Melissa and “I Love You” outbreaks as a twenty-something Toronto Stock Exchange analyst launched his pivot into information security.

The conversation turns to leading at scale. Rob walks through the three mentors who shaped him — “the teacher” who grounded him in fundamentals at Bank of Montreal, “the coach” who taught him the collaborative nature of global operations at Scotiabank, and “the general” who sharpened his leadership edge. He frames these not as phases but as lenses he still applies situationally today.

Rob and Steve dig into incident response — from taking down Canada’s first phishing site with no playbook to running tabletop exercises at the board, C-suite, and technical levels. Rob argues every organization needs a breach coach and that communications is the biggest make-or-break factor in a breach. He also offers a candid take on CISO politics — short tenures, CIO friction, and why trust with your boss matters more than being right.

The episode closes with Rob’s take on why this may be the best time in history to be a new CISO. AI is stripping away the commodity work that defined earlier generations of the role, leaving more room for strategy, leadership, and real influence. For anyone stepping into the seat, Rob’s message is simple: the most valuable skills aren’t technical at all.

Key Topics

• Rob’s path from a VIC-20 and a grade-school BBS to the CISO seat

• How DJing as “Robbie Knobs” clinched his first big bank interview — and why “notables” matter on a resume

• Taking down the first phishing website in Canada with no playbook and a lot of cold calls

• The three mentors who shaped his leadership: the teacher, the coach, and the general

• Why tabletop exercises at the board, C-suite, and technical levels each matter — and how they differ

• The case for engaging a breach coach before a breach happens, not during one

• Why communications is the single biggest make-or-break factor in incident response

• How AI is reshaping the CISO role by stripping away commodity work

Guest

Rob Knoblauch — Chief Information Security Officer

Rob Knoblauch is a seasoned CISO with 25+ years of global information security leadership. He began his career at the Toronto Stock Exchange during the Y2K era and later held increasingly senior roles at Bank of Montreal and Scotiabank, where he spent years as Deputy CISO and VP of Global Security Services. Rob is also a startup advisor and longtime house music DJ performing as “Robbie Knobs.” Connect with Rob on LinkedIn.

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What does sharpening a knife over a case of onions have to do with incident response? For Myke Lyons, CISO at Cribl, the answer is everything. Myke trained at the Culinary Institute of America — learning speed and accuracy under the clock of a professional kitchen — before a summer IT job in Manhattan set him on an entirely different path. In this episode of The New CISO, host Steve Moore traces that journey and the surprising parallels between culinary craft and security leadership.

The conversation moves through a career that evolved organically: a summer job moving refrigerator-sized printers in a Manhattan ad agency, a crash course in executive white-glove IT support, a breakthrough moment finally cracking subnetting, and a slow expansion from NOC operator to global security leader. Myke credits the kitchen — its insistence on precision and calm under fire — for instilling an operator's mindset that still defines how he leads through incidents today.

Mentorship, both formal and accidental, threads through Myke's story. A curmudgeonly colleague who threatened to "replace him with a script" taught him the value of continuous improvement. A trusted mentor reframed the CISO's role with a single line about house fires and lock changes. And years in executive IT support gave Myke an early education in empathy and knowing when not to fix what wasn't asked.

Myke and Steve examine a vendor incident where a product leader's dismissive response to a forensics question destroyed credibility with hundreds of customers. The lesson: saying "I don't know, but we'll find out" is not a weakness — it is the most powerful tool a leader has. The same insight applies to M&A due diligence, where reframing technical conversations as expectation-setting exercises turns adversarial interviews into collaborative ones.

For Myke, the new CISO is defined by empathy and culture. Know your audience. Think like your customers. Communicate policy changes as explanations, not mandates. Find your internal advocates and invest in them before you need them. The recipe for great security leadership is less about technology than it is about people — and that lesson translates perfectly from the kitchen to the boardroom.

Key Topics

• Career pivots: from culinary school to IT and cybersecurity

• Speed, accuracy, and craft — what kitchen discipline teaches security professionals

• Building an operator's mindset and staying calm during security incidents

• White-glove executive IT support and the patience, precision, and empathy it develops

• Mentorship — formal and accidental — and the lessons that only land in retrospect

• The dangers of filling silence with false confidence vs. the power of saying "I don't know"

• Crisis communication best practices and what not to do during a vendor incident call

• Managing M&A security due diligence with low-emotion, expectation-setting conversations

• Building security culture through empathy, clear communication, and internal advocates

• Telemetry, log management, and Cribl's role as the data engine for IT and security

Guest Bio

Myke Lyons is the Chief Information Security Officer at Cribl, the AI platform for telemetry trusted by organizations worldwide — including half of the Fortune 100 — to manage IT and security data at any scale.

He trained at the Culinary Institute of America with aspirations of becoming a food critic — until a summer IT job in Manhattan set him on an entirely different course. Myke went on to build expertise across networking, NOC operations, and log management, holding CISO positions at Snyk and Collibra before joining Cribl in 2024.

Connect with Myke on LinkedIn and learn more about Cribl at cribl.io.

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Alan Lucas always wanted to be an architect or a firefighter — as CISO of Worldstream and Greenhouse Datacenters, he has become both. In this episode, he joins host Steve Moore to explore leading cybersecurity at the intersection of design and crisis response.

Alan traces his path from Fox-IT through a Dutch cryptocurrency exchange where he arrived post-breach to an organization under near-constant attack from nation-state threat actors. Leading a technically sophisticated but security-anxious leadership team, he learned the lasting power of transparency and directness — and his most memorable measure of success was not a technical control, but a CTO who finally slept through the night.

The conversation goes deep into crisis communication. Alan and Steve discuss how the industry has matured from reflexive silence around breaches to embracing transparency as a trust-building tool, the danger of well-meaning legal edits that send customers chasing the wrong narrative, and why the CISO should hold final review over all public incident communications. He also shares his Security Champions Program, tabletop exercise design, and why knowing who to call in a crisis must be mapped out before that crisis arrives.

Alan also covers his volunteer work with the DIVD, coaching ethical hackers and supporting responsible disclosure worldwide — an extension of his belief that security, done well, creates trust and enables growth for everyone.

The episode closes on "bouncing forward" — the idea that true resilience means using every incident as a forcing function for improvement, not just a return to baseline. Alan frames lessons learned as the most important resilience KPI a security team can own. A masterclass in leading through both calm and chaos.

Key Topics

• The architect-and-firefighter mindset: building security programs while fighting live fires

• Alan's career path from Fox-IT (MSSP) to post-breach CISO at a cryptocurrency exchange

• Leading security post-breach — and what "sleeping well again" actually means

• The unique threat landscape facing cryptocurrency companies, including nation-state adversaries

• The Dutch Institute for Vulnerability Disclosure (DIVD): coordinated, ethical vulnerability disclosure worldwide

• Mentoring young ethical hackers: communication, confidence, and responsible disclosure process

• Crisis communication: balancing transparency with operational security during active incidents

• Why legal edits to breach notifications can mislead customers and create dangerous distractions

• The CISO's role as final reviewer of all incident communications

• Security Champions Programs: bridging the gap between security and non-technical departments

• Tabletop exercise design: running effective simulations in under an hour with non-technical staff

• Writing the breach notification letter before the breach happens

• Bouncing forward, not bouncing back: using lessons learned as a resilience KPI

• Security as a business enabler: positioning the CISO role for organizational growth and confidence

Guest Bio

Alan Lucas is CISO at Worldstream and Greenhouse Datacenters, two of the Netherlands' leading cloud and data center infrastructure providers. With over a decade of cybersecurity experience, he leads security strategy for mission-critical IT and cloud environments. Prior roles include Fox-IT (MSSP) and LiteBit, a Dutch cryptocurrency exchange where he served as CISO post-breach. Alan also volunteers as a coach at the Dutch Institute for Vulnerability Disclosure (DIVD), mentoring ethical hackers and supporting responsible disclosure globally. He is passionate about security as a catalyst for innovation — and about building a safer digital society, one step at a time.

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In this episode of The New CISO, host Steve Moore speaks with Dean Sapp, CISO and Data Protection Officer at Filevine, about one of security's most critical yet overlooked skills—written communication. Drawing from a brutal college English class that failed students for a single typo and over 20 years building security programs in the legal tech industry, Dean reveals why the ability to articulate security findings clearly separates average professionals from exceptional leaders who drive real business impact.

After abandoning architecture when he learned it would take six years to become licensed, Dean leveraged his dual skills in computer-aided drafting and IT to launch a career at Novell, eventually earning nine certifications in two years and a master's degree from SANS Institute. His background in design thinking shapes how he approaches security program development—viewing it like building a structure that requires solid foundations, functional systems, and even window dressing like SOC 2 compliance.

After interviewing over 100 candidates for SOC positions, Dean identifies the biggest missing skill as the inability to translate security findings into business language executives understand and act upon. He introduces the BLUF (Bottom Line Up Front) principle from military communications, explaining why security professionals have roughly eight seconds to capture executive attention. Dean champions radical transparency through simple frameworks—using stoplight systems or report card grades to communicate security posture, deliberately giving his own program failing marks in areas needing improvement to build trust.

Dean tackles operational communication breakdowns that create real security risk, emphasizing mandatory peer review before escalating incidents. This two-person rule dramatically improves report quality while reducing false positives that waste senior leadership time. He shares how this high-standards approach helped Filevine achieve best-in-class cyber insurance rates, with underwriters calling their security program superior to any SaaS provider they'd evaluated. Drawing on Erik Durschmied's "The Hinge Factor," he illustrates how small communication failures doom missions—just as cavalry troops charging cannons failed because not one rider carried the nails and hammer needed to disable them.

Throughout the discussion, Dean emphasizes holding yourself to impossibly high standards so that external auditors find you excellent. He advocates for brutal honesty about program gaps, documenting accepted risks clearly, and using tools like Grammarly Premium to improve writing quality. His philosophy combines military precision, architectural thinking, and pedagogical discipline—all in service of making security programs that actually work rather than just looking good on paper.

Key Topics Discussed:

* Why written communication is security's most critical missing skill

* BLUF (Bottom Line Up Front): Capturing executive attention in 8 seconds

* Using stoplight or report card systems for transparent board reporting

* Giving your security program honest grades to build executive trust

* Mandatory peer review before escalation to reduce false positives

* How Filevine achieved best-in-class cyber insurance rates

* The two-person rule for improving incident report quality

* Lessons from "The Hinge Factor" about preparation and tools

* Holding impossibly high standards so external auditors find you excellent

* Translating technical findings into business impact language

LEARN MORE:

👉 LinkedIn: https://www.linkedin.com/in/deansapp

Company Website: https://www.filevine.com

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In this episode of The New CISO, host Steve Moore speaks with Manuel "Manu" Ressel, CISO at SAUTER Group, about his unconventional journey from classroom teacher to cybersecurity leader—and why the "Four Cs" of modern education provide a powerful framework for building effective security programs. Drawing from years as both a teacher and school principal in Germany, Manu introduces Critical Thinking, Communication, Collaboration, and Creativity as essential leadership skills that fundamentally challenge how the industry approaches awareness training and incident response.

After growing frustrated with Germany's outdated education system that prioritized memorization over critical thinking, Manu left his position as principal and reinvented himself as a digital transformation consultant. Working with schools and mid-sized companies to adopt cloud technologies, he eventually landed the CISO role at SAUTER, an international building automation company with 4,000 employees across multiple countries.

The conversation tackles security's most persistent failure: awareness training that doesn't work. Manu reveals that 37% of security incidents in Germany could be prevented if users made better decisions, yet most organizations rely on boring click-through programs. He advocates for scenario-based, role-specific training—an approach now mandated by Europe's NIS 2 regulation—that treats people as the biggest opportunity in cybersecurity rather than the weakest link.

One of the episode's most practical frameworks is Manu's Observation-Description-Interpretation method for analyzing security incidents. He explains how humans naturally jump from observation directly to interpretation, skipping the crucial middle step of accurately describing what actually happened. This leads to finger-pointing, misdiagnosis, and hasty decisions. By training security analysts to pause and describe incidents factually first, teams make better decisions and build trust with the business.

Manu challenges the punitive approach many organizations take toward security failures, particularly companies that fire employees for repeatedly clicking phishing simulations. He champions building positive fault cultures where employees feel safe reporting mistakes. His three crisis questions—Is anyone dying? Major financial impact? Will someone be hurt?—provide a simple framework for staying calm and deciding when immediate action is necessary versus taking time to think strategically.

Key Topics Discussed:

1. Why the "Four Cs" (Critical Thinking, Communication, Collaboration, Creativity) define effective security leadership
2. The Observation-Description-Interpretation framework for incident analysis without bias
3. Transforming ineffective awareness training into engaging, scenario-based programs
4. Building positive security cultures where employees report issues without fear
5. NIS 2's mandate for role-specific cybersecurity training across organizational levels
6. Why Germany and European mid-market companies lag in cloud adoption
7. Three critical crisis questions: Is anyone dying? Financial impact? Risk of harm?
8. Why punitive phishing training destroys trust and cultural engagement
9. Applying teacher skills to security leadership and de-escalation techniques
10. Staying calm as a CISO's most important superpower during incidents

LEARN MORE:

👉 Guest LinkedIn: https://www.linkedin.com/in/manuel-ressel-9279b997/

Company website: https://www.sauter-controls.com/

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In this episode of The New CISO, host Steve Moore speaks with Alex Rice, Founder, CTO, and CISO at HackerOne, about challenging one of cybersecurity's most deeply held beliefs—that security should be the top priority. Drawing from his journey building security programs at Facebook and founding HackerOne, Alex introduces the "safety third" philosophy and explains why accepting that security is never first can actually make you more effective as a leader.

Alex shares his unconventional path into cybersecurity, starting as a 14-year-old programmer in rural Florida and eventually leading product security at Facebook during its explosive growth. He reveals how Facebook ran 70+ penetration tests annually with top-tier vendors and still wasn't finding enough vulnerabilities—until they opened the doors to the hacker community and received over 300 valid findings in a single weekend. This experience became the foundation for HackerOne's bug bounty platform.

The conversation tackles critical leadership challenges facing modern CISOs, including the toxic tendency toward victim blaming when breaches occur, why security teams struggle with customer-centric design, and how to avoid becoming the team everyone knows only for blocking work and sending phishing tests. Alex argues that security professionals must stop drinking their own Kool-Aid and recognize that usability and business outcomes will always take precedence over security controls.

In the episode's second half, Alex addresses AI's role in security operations with refreshing pragmatism. Rather than chasing grandiose AI visions, he advocates for starting with narrow, well-defined tasks where agents can replace security toil—like automated CVSS scoring or vulnerability triage—building trust and expertise before tackling more ambitious projects. He warns against the current trend of AI tools that find more problems when security teams desperately need help fixing the mountain of issues they already know about.

Alex also challenges CISOs to stop over-owning problems like asset inventory management that rightfully belong to other executives, emphasizing the importance of cross-functional collaboration over building security-owned solutions that ultimately fail. Throughout the discussion, he champions a philosophy of empathy, customer-centricity, and accepting hard truths about security's actual place in business priorities—a mindset shift that paradoxically makes security leaders far more effective.

Key Topics Discussed:

1. Why "safety third" should be every CISO's operating philosophy
2. The problem with victim blaming in cybersecurity incidents
3. Building customer-centric security programs that enable rather than block
4. Lessons from scaling Facebook's security program with 70 pen tests per year
5. The origin story of HackerOne and crowdsourced security testing
6. How to avoid becoming the security team everyone resents
7. Practical AI implementation: Starting with toil elimination, not transformation
8. Why CISOs over-own asset management and other problems
9. The importance of process mapping before deploying AI agents
10. Aligning security teams closely with AI and software development

In this episode of The New CISO, host Steve Moore speaks with Iain Paterson, Chief Information Security Officer at Well Health Technologies, about his unconventional path into cybersecurity and the lessons learned from building programs across industries—from banking and healthcare to breach response and beyond.

From skipping college to take an eight-month technical boot camp to leading enterprise security programs, Iain shares how curiosity, hands-on experience, and communication skills shaped his journey. He opens up about the realities of hiring in cybersecurity, why foundational IT work still matters, and how soft skills like empathy and composure are essential for effective leadership. Iain also reflects on leading through high-stress incidents, including the Ashley Madison breach, and explains why staying calm, communicating clearly, and maintaining emotional intelligence define the “new CISO.”

Key Topics Covered:

• A nontraditional start: skipping college for certifications and hands-on learning
• Why technical foundations—servers, networks, and support—still matter
• The problem with “boilerplate” resumes and lack of real-world experience
• Why soft skills are a security superpower: communication, patience, and empathy
• Transitioning from technician to business enabler in cybersecurity
• How early help desk experience builds composure and problem-solving ability
• Lessons from running vulnerability management in large-scale banking
• Learning resilience and resourcefulness as a one-person security team in healthcare
• Behind the scenes of the Ashley Madison breach: stress, responsibility, and empathy
• Why composure, calm communication, and credibility matter in crisis response
• The leadership evolution from technical expert to executive decision-maker
• Building peer networks and finding mentorship to combat isolation as a CISO

Iain’s story highlights how real experience, emotional intelligence, and community support transform good technologists into exceptional leaders. His insights remind us that cybersecurity isn’t just about defense—it’s about communication, composure, and connection.