The Watchtower

As AI accelerates the pace of cybersecurity and pushes more complex decisions onto security professionals, managing burnout is becoming an essential leadership skill.

Bronwyn Boyle, CISO at PPRO, and Don Gibson, cybersecurity leader at Anglo American, explore how AI is changing the cognitive demands of cybersecurity, why even experienced leaders can miss the signs of burnout, and how psychological safety, better workplace practices, and a no-blame culture can help build more resilient security teams.

In this episode of The Watchtower, they join host Ash Hunt to discuss how expectations of CISOs are changing, why acknowledging burnout is no longer necessarily a sign of weakness, and what it takes to create a security culture that supports its people rather than simply asking them to withstand more pressure.

Connect

Bronwyn Boyle on LinkedIn

Don Gibson on LinkedIn

Ash Hunt on LinkedIn

Chapters

00:00 Is Calling Out Burnout a Career Risk?
03:40 How Cybersecurity Leadership Has Changed
05:58 AI and the Growing Pressure on CISOs
10:06 How AI Is Shifting Cognitive Load
14:08 New Threats and Changing Security Practices
16:50 The Evolving Role of the CISO
18:37 Recognizing the Warning Signs of Burnout
23:06 The Personal Cost of Cybersecurity
27:14 Creating a Culture of Psychological Safety
31:02 Supporting Teams Through Pressure
34:52 Rethinking How Security Teams Work
37:04 The Exhausting Pace of Change
41:58 Building a No-Blame Security Culture
45:09 Practical Ways to Manage Stress and Burnout
49:47 Why Community and Peer Support Matter

Presented by Cyera. Produced by Mission.org.

Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

Are we building enterprise AI backwards? As organizations race to adopt bigger, more powerful AI models, Alex Attumalil, Global CISO at Under Armour, believes the real transformation may come from thinking smaller.

In this episode of The Watchtower, Alex joins Ash Hunt to explore why general-purpose LLMs aren't enough to transform complex business processes, how smaller, specialized AI models could reshape the enterprise, and why business leaders, rather than technology teams, should be driving AI adoption.

They also examine how AI is changing cybersecurity itself. From sophisticated phishing attacks that are forcing organizations to rethink decades of security training to AI-powered security operations that can deliver faster, more consistent decisions, Alex shares how security leaders must adapt to a rapidly changing threat landscape.

And as automation continues to evolve, what happens when AI can identify software vulnerabilities before they ever reach production?

Connect

Alex Attumalil on LinkedIn

Under Armour

Ash Hunt on LinkedIn

The Watchtower

Learn More

datasecAI by Cyera

Chapters

0:00 One giant brain, or lots of small ones?
1:18 Meet Alex Attumalil, Global CISO at Under Armour
2:19 The two-front war: defending AI, and defending against AI
4:47 The decade of phishing training that just became obsolete
7:32 Running security consistently across a global business
10:38 The only SecOps metric that matters: time to action
15:32 'Democratizing the response' — AI's hidden payoff
16:53 Why your tech team is the wrong owner for AI
22:44 The micro-LLM thesis: enterprise AI as microservices
24:53 Repatriation: bringing tuned AI back into the data center
25:30 Why LLMs keep giving you different answers
28:14 SLMs are quietly beating LLMs in the enterprise
30:52 Where the CISO role goes next
34:44 Could software ever have no vulnerabilities?
37:05 Every enterprise does two things. The rest is scaffolding.

Presented by Cyera. Produced by Mission.org.

Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

If Convenience Wins, We Lose.

Evan Gordenker led more than 160 insider investigations at Unit 42, including work on DPRK IT-worker operations, before taking over insider threat and data security at Airwallex.

Evan joins Ash Hunt to showcase how intent is often the wrong place to start. Whether the risk comes from an employee, an AI agent, or an adversary using legitimate credentials, the real question is what trusted access allows them to do.

Evan explains why convenience sits at the center of human and agentic risk, how AI agents expose the limits of access models built for people, why security teams need finer-grained control over credentials and permissions, and why the DPRK IT-worker playbook keeps working without changing much at all.

Connect

Evan Gordenker on LinkedIn

Airwallex

Chapters

0:00 The insider threat you're worried about isn't a person
1:19 How Evan fell into cybersecurity via the Tokyo Olympics
4:20 What the industry gets wrong about who the insider actually is
5:25 Why the 'secret police' framing kills your program
8:00 Intent doesn't matter — controls do
9:30 What a real, messy insider investigation actually looks like
12:30 One sentence in an incident report can end a career
15:01 Would you classify an AI agent as an insider?
16:33 The one-password experiment — how agents test every credential
19:39 4 years into agentic systems. Still built for humans only.
23:54 If security runs insider risk alone, you're toast
28:35 The DPRK IT-worker threat — and why it hasn't had to evolve
32:54 How Fortune 500s started frustrating North Korean operators
36:48 The one through-line: convenience
42:50 Why InfoSec has never mattered more than right now

Presented by Cyera. Produced by Mission.org.

Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

Should detection and response remain the center of security when AI, data, and identity are converging at machine speed?

Detection and response has long been an organizing principle of enterprise security. Francis Odum, Founder and CEO of Software Analyst Cyber Research, argues that model is being pushed to its limits as AI agents act autonomously and attack timelines compress.

In this episode, Francis and Ash Hunt explore why existing identity controls may not be enough for AI agents, why every AI security vendor sounds identical right now, and how security controls have to change for agentic systems.

Connect

Francis Odum on LinkedIn

Software Analyst Cyber Research

Ash Hunt on LinkedIn

Chapters

0:00 Can Human-Speed Security Stop Machine-Speed Threats?
1:15 Francis Odum on What's Changing in Cybersecurity
3:53 Cybersecurity Was Built for Humans — Not Agents
8:44 Why Every AI Security Vendor Sounds the Same
11:08 Why Platforms May Win the AI Security Race
14:31 What Happened to the First Wave of AI Security Startups
19:20 Why Non-Human Identities Were a "Head Fake"
22:00 Should AI Agents Have Their Own Identity?
25:58 The Authorization Problem AI Agents Create
28:29 What Hugging Face Revealed About Agent Controls
32:15 Can Detection and Response Keep Up With AI?
34:27 How AI Makes Attacks Faster and Cheaper
36:02 Why Security Has to Become More Preemptive
41:03 The New Agentic Supply Chain Risk
43:27 Why Agentic Failures May Not Look Like Cyberattacks
45:13 What SACR Is Researching Next

Presented by Cyera. Produced by Mission.org.

Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

If you focus entirely on the external AI-fraud threat, you're going to get burned by what's already inside your organization.

AI is making external fraud more convincing - deepfake CEOs on service-desk calls, synthetic video, generative BEC. But the same tools also scale internal fraud, from fake invoices and fabricated expenses to ghost employees.

Mason Wilder, Research Director at the Association of Certified Fraud Examiners, joins Ash Hunt to unpack why it's never been easier to commit fraud, how organized crime is changing the landscape, and why the old walls between cybersecurity, fraud, and AML are starting to break down - and where companies should actually be investing to keep up.

Connect

Mason Wilder on LinkedIn

ACFE

ACFE Anti-Fraud Technology Benchmarking Report

ACFE Report to the Nations

Chapters

0:00 The AI Fraud Threat Inside Your Company
1:03 From Overnight SOC Shifts to the ACFE
2:56 Why Fraud Has Never Been Easier
4:55 What the 2026 AI-Fraud Survey Revealed
5:25 Why Only 7% Feel Prepared for AI-Powered Fraud
6:12 Why Cyber, Fraud, and AML Can't Stay Siloed
9:33 How Deepfake Fraud Started in 2018
11:54 From Social Engineering to Automated Attacks
13:41 Where Companies Should Invest Against AI Fraud
16:53 The Internal Fraud Risk Getting Overlooked
20:00 Why Internal Fraud Doesn't Go Away
22:52 Why Tips Still Catch 43% of Fraud
26:18 Turning Employees Into a Fraud Detection Layer
28:17 What Agent-to-Agent Fraud Changes
34:59 How Singapore Is Shifting Fraud Liability
37:11 What Deepfake Detection Really Looks Like
42:24 Why Cyber and Fraud Are Ultimately on the Same Team

Presented by Cyera. Produced by Mission.org.

Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

When security deals in absolutes, the business finds a way around it.

Bose CISO Arun Abraham joins Ash Hunt to discuss why flat “no”s create shadow IT, how security leaders can enable AI without opening the gates, and why fundamentals like data, identity, vulnerability management, and risk prioritization still matter most.

Connect

Arun Abraham on LinkedIn

Bose Corporation

The Watchtower

Chapters

0:00 Are We Too Secure?

1:25 The CISO outsider advantage

5:19 Puritanism in security

6:24 How to earn trust when you tell executives the truth

8:11 Why quantitative risk beats maturity curves

9:39 The three fundamentals: detect, respond, VM

13:44 What AI enablement requires from security

14:14 The cloud playbook applies: enable or get shadow AI

15:10 The CISO who got replaced for saying no

15:49 Why Bose's security team has a backlog

19:59 The five-minute aha moment

21:34 If you don't know where your data is, you can't enable AI

25:09 The internal AI agent that replaced policy

27:22 The secure SDLC didn't look like this five years ago

29:44 AI won't invent new attacks - it'll use your deficiencies

31:04 Perfect is the enemy of good

Presented by Cyera. Produced by Mission.org.

Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

Is security really failing or is it our Paleolithic brains?

It’s the 'responsibility-control paradox' eating CISOs alive

Peter Coroneos is the founder of Cybermindz.org, former head of Australia's Internet Industry Association, and one of the few voices in cybersecurity trained in both law and neuroscience. In this episode he explains why we're running paleolithic brains inside a 21st-century attack surface, why the industry's definition of 'resilience' is quietly draining its best people, and why AI is about to accelerate burnout before it eases it.

Connect

Peter Coroneos on LinkedIn

https://cybermindz.org/

The Watchtower

Chapters

0:00 Is security really failing? Or are our paleolithic brains?

2:07 The brain in a bucket: how it all started

3:41 From neuroscience to internet law to cyber policy

4:50 Why Peter started seeing burnout in his peers pre-COVID

8:28 Alert fatigue and vigilance decrement inside the SOC

11:31 Paleolithic brain, meet 21st-century attack surface

11:55 The signal your brain never gets: no cue to de-escalate

12:09 The responsibility-control paradox that breaks CISOs

14:23 Why your brain can't tell virtual threat from physical

16:52 Stress takes your prefrontal cortex offline

18:53 Why Cybermindz stopped talking about wellness

20:00 Burnout is a lagging indicator

28:24 What actually changes inside teams that get support

28:46 Stress you can sustain if you design in recovery

38:35 Your best analysts don't lose skills. They lose access.

41:17 The AI accelerant: why burnout is about to get worse

45:44 What CISOs should do before the gap opens up

Presented by Cyera. Produced by Mission.org.

Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

How defense keeps up with AI, cyber threats, and private-sector innovation.

In this episode of The Watchtower, Ash Hunt sits down with Jimmy Harrington, retired Air Force colonel and former Deputy CIO at U.S. Special Operations Command, for a conversation about cyber resilience, defense innovation, and what large organizations often misunderstand about speed.

From NATO and the Pentagon to AI-enabled defense systems and private-sector collaboration, Jimmy shares what defense can teach enterprise security leaders about resilience, leadership, mentorship, and building organizations that can operate through uncertainty.

Highlights

• Why “keeping up” may be the wrong question
• How zero trust changes the goal from prevention to resilience
• Why defense innovation can become “innovation theater”
• What it takes for new technology to actually scale
• What CISOs can learn from military leadership and mentorship

Connect

Jimmy Harrington on LinkedIn

Chapters

0:00 Can organizations keep up with innovation?

1:14 Jimmy Harrington Deputy CIO

5:36 The pace problem inside defense institutions

6:50 Reframing cyber success: stop trying to stop everything

8:49 Run fast, trip less - operating under uncertainty

12:12 Threat-agnostic vs threat-specific cyber defense

14:09 Defense tech: from leading edge to catching up

15:14 Innovation theater: the $5B that never scaled

18:55 Slow is smooth, smooth is fast

21:16 Palantir, Anduril, and selling belief to the DoD

24:33 Building the plane while it's flying

27:23 Why CISOs and defense leaders don't collaborate enough

31:34 The military's leadership DNA corporate lacks

35:49 Mentorship and the replacement-first model

41:24 How leaders are actually built

43:10 The hardest part of leaving the military

46:28 What corporate underestimates about veterans

Presented by Cyera. Produced by Mission.org.

Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

Is AI helping us make better decisions or just giving us more data to misinterpret?

In this episode of The Watchtower, Ash Hunt speaks with Tony Martin-Vegue, founder of NinetyFive Risk Advisory and author of From Heat Maps to Histograms, about cyber risk, decision-making, and the role of AI in risk analysis.

Tony explains why security teams often have more data than they realize, but still need the judgment to evaluate that data, understand its quality, and use it responsibly.

Highlights

• Why AI can supercharge risk analysis without replacing human judgment
• How LLM outputs should earn their way into a risk model
• Why red/yellow/green heat maps limit executive risk conversations
• How cyber risk quantification helps security leaders speak in business terms
• What cybersecurity can learn from meteorology, epidemiology, actuarial science, and financial risk management

Connect

Tony Martin-Vegue on LinkedIn

95 Risk Advisory

Chapters

0:00 The judgment problem AI can't solve

1:24 From IT janitor to risk analyst with Tony Martin-Vegue

5:19 Explaining risk in dollars vs colors

9:35 Not enough data is not an excuse

13:50 The DBIR, data quality, and the 500-report flood

16:46 Industry reports or Twitter polls

17:39 Decision engineering: operating under uncertainty

20:35 The CISO's real job isn't stopping attacks

21:31 The most influential cybersecurity book

28:41 AI launders bias

31:49 Decision engineering at scale: agentic context across the business

39:43 Cyber risk math was invented by 18th-century gamblers

41:20 What cybersecurity needs to steal from other fields

43:44 Toyota, Taylorism, and why your heat map has to die

45:53 Where to find Tony and the book

Presented by Cyera. Produced by Mission.org.

Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

Identity is now the fabric that determines the viability of every business operation.

In this episode of The Watchtower, Ash Hunt talks with Valvoline CISO Corey Kaemming about how identity became the operational backbone of modern companies. As cloud, automation, and AI accelerate, identity failures don’t just create risk - they stop work entirely. They explore why identity decisions are now business decisions, how automation amplifies identity risk, and why CISOs are evolving from gatekeepers into service leaders responsible for keeping operations moving.

Chapters

0:00 Identity Now Runs Everything (Corey Kaemming)

1:20 Why Identity Suddenly Matters More Than Ever

5:40 “Attackers Aren’t Breaking In… They’re Logging In”

9:30 Identity as the Backbone of Enterprise Operations

12:00 You Can’t Just “Turn On” AI in Security

17:00 Moving Beyond Passwords - What Users Actually Want

19:20 Why Identity Workflows Keep Breaking

23:10 When Identity Fails, the Business Stops

26:00 “If You Can’t Log In, Nothing Works”

29:10 Inside a Real Identity Transformation Program

34:50 Who Should Own Identity - Security or the Business?

41:30 Rethinking Hiring, Teams, and Identity Strategy

46:15 Identity Beyond Security

Presented by Cyera. Produced by Mission.org.

Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

Security runs on metrics, but do those metrics reflect real risk?

In this episode of The Watchtower, Ash Hunt sits down with Wade Baker - co-founder of Cyentia Institute and longtime architect of the Verizon DBIR - to dismantle the cybersecurity metrics that feel right but consistently lead programs astray. They take down "average cost per breach," expose why MTTR makes security teams look great while 99% of their vulnerabilities sit untouched, and introduce the half-life metric that actually tracks risk. Plus: why metrics are weaponized more often than they're used, and how AI agents are (finally) democratizing rigorous risk quantification.

Key Takeaways:

- Cost-per-data-record is a survey artifact — there's no linear correlation between breach cost and records lost

- MTTR only measures the vulnerabilities you remediate — so you can post a great MTTR while ignoring 99% of your environment

- Survival analysis / half-life is the better metric — it tracks burn-down against a defined finish line, not raw speed

- Think like a general, not a sniper: zero vulnerabilities is the wrong objective; the right 80% is

- Metrics are weaponized to justify budget more often than they're used to manage program effectiveness

- You don't need a stats PhD — AI agents are democratizing rigorous risk modeling

Wade Baker on LinkedIn: https://www.linkedin.com/in/drwadebaker/

Cyentia Research: cyentia.com/research

Chapters

00:00 Are we measuring the right things?

01:18 Which cybersecurity metrics are most misunderstood

02:48 The psychology of measuring what's easy

04:20 "We've got to measure something" — and the trap that creates

05:30 The real problem: security doesn't agree what "good" looks like

07:40 Sniper vs general: the thinking style CISOs need

09:28 Doing security things vs achieving security goals

10:25 The $215-per-record myth — and why it won't die

12:13 Metrics as weapons: the real reason the number survives

14:31 The needle-in-the-haystack reality of real breaches

15:45 Risk quantification was solved decades ago — in other industries

17:24 The MTTR indictment: measuring only what you fix

18:48 Survival analysis and the half-life metric

21:07 Fixed-speed decay: metrics as decision engineering

23:57 Event landscape vs threat landscape

27:19 AI agents as scenario-analysis partners

30:05 Democratizing risk modeling without a stats PhD

31:13 What security leaders should actually measure

34:15 Your metrics are not your boss's metrics

36:07 Data storytelling: testing a metric's "so what?"

37:03 What's next from Cyentia Institute

Presented by Cyera. Produced by Mission.org.

Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

Are you just avoiding a breach? Or are you prepared for one?

Dan Bowden is the Global CISO at Marsh - the world's largest insurance broker - where he protects 90,000+ employees across 130+ countries while simultaneously seeing how organizations are evaluated after cyber incidents. In this episode, Dan breaks down how regulation, insurance, and real breach data are changing the standard for what "prepared" actually means in 2026.

Dan Bowden is a seasoned security leader with a background spanning military, healthcare, and banking before joining Marsh as joint Global CISO.

Key takeaways:

- Why the gap between governance documentation and crisis culture is where most organizations fail

- How to properly engage your cyber insurance broker as a consultative security partner, not a checkbox

- What Marsh's breach data actually shows about insured companies being targeted (spoiler: the myth is busted)

- Why MFA in 2026 should be baseline - and what carriers are asking about next

- How regulatory frameworks like NYDFS are shifting from descriptive to prescriptive requirements

Guest: Dan Bowden, Global CISO, Marsh

LinkedIn: https://www.linkedin.com/in/deltasbravo/

Chapters

0:00 Dan Bowden: Cybersecurity Is Not “Best Effort”

1:10 What a Global CISO Sees That Others Don’t

3:50 Why Companies Call Their Broker First During an Incident

5:03 What Real Incident Data Actually Teaches You

7:04 Rethinking Risk: Frequency vs Catastrophic Events

10:12 Why Cyber Risk Is Still Measured Wrong

11:39 Stop Letting the News Drive Your Security Strategy

14:32 Where Incident Response Actually Breaks Down

15:00 Governance vs Culture - What Really Happens in Crisis

18:03 How to Test Leadership Under Pressure

19:32 What Most Companies Get Wrong About Cyber Insurance

23:12 Cyber Insurance Is Bigger Than “Cyber”

24:11 Why Most Broker Relationships Fail

25:52 How Insurance Decisions Actually Get Made

27:53 Identity Is the Root of Most Attacks

29:46 MFA Is the Baseline - But Not the End

33:27 How Regulation Is Reshaping Security

37:52 Myth: Insurance Makes You a Target

41:31 The Future: Custom Cyber Insurance Models

Presented by Cyera. Produced by Mission.org.

Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

We’ve spent billions on cybersecurity. Why are the problems the same?

In the first episode of The Watchtower, Ash Hunt invites Jason Clark, CSO at Cyera, to dig into the hard truth that foundational security controls still fail in real environments. Together, they explore why identity and data remain unsolved, how rapidly changing enterprise tech has outpaced control design, and why AI is forcing the industry to rethink its entire foundation.

This episode is made possible by Cyera.

Chapters

0:00 Has Cybersecurity Failed?

1:22 Jason Clark - Security Built for Old Tech

2:48 Why Security Frameworks Keep Failing

4:58 The Pattern - We Can’t Keep Up - iPhone, Cloud, AI Adoption

7:47 Security Strategy Problem - No Data Visibility

10:02 Data and Identity Are Broken in Security

13:34 Identity Is a House of Cards

15:09 AI Will Break (or Fix) Cybersecurity

18:18 Rethinking Security - Systems and Data as Assets

20:39 Why Security Teams Clash with the Business

24:02 Why Risk Modeling Fails in Security

27:58 CISO Leadership Problem - No Business Influence

30:42 AI Adoption - Why Security Must Lead

33:17 The Future of Cybersecurity - Orchestrating Intelligence

34:07 Closing - What Comes Next

Presented by Cyera. Produced by Mission.org.

Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

The systems we rely on weren’t built for the world we’re running today.

Welcome to The Watchtower.

The cybersecurity podcast exploring how identity, data, and behavior now control whether a business runs - or stops.

Hosted by former global CISO, Ash Hunt, The Watchtower pulls back the curtain on what’s actually happening behind dashboards - from fragile identity systems to the real impact of AI inside the business.

New episodes coming soon.

Presented by Cyera. Produced by Mission.org.

Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.