In this episode, Steve Malone, Chief Product and Strategy Officer at IRONSCALES, joins the podcast to unpack how the threat has evolved through what IRONSCALES calls “Phishing 3.0,” and what security leaders should actually be doing about it. Steve has spent two decades in email security, including senior product leadership roles at Mimecast and Egress, giving him a front-row seat to how attacks, and defenses, have changed.

Topics covered:

• Why speed and quality, not new attack methods, are what’s really changed about phishing

• What IRONSCALES’ 2025 Cost of Phishing report reveals about the gap between faster incident handling and rising overall costs

• The evolution from phishing 1.0 (malicious attachments) to 2.0 (BEC and social engineering) to 3.0 (AI-generated, multi-channel attacks)

• Why old advice like “spot the typo” or “call to verify” no longer holds up against deepfakes

• How Ironscales’ native API integration, adaptive AI and Agentic Virtual SOC reduce the volume of incidents reaching human analysts

• IRONSCALES’ red teaming agent, and how it powers hyper-personalized detection and security awareness training

• Real-time deepfake detection for Microsoft Teams meetings, and the emerging threat of deepfakes in recruitment

• Steve’s advice for CISOs on rethinking security metrics, hardening business processes and questioning vendors about their AI capabilities

Daniel Blackford, VP and Head of Threat Research at Proofpoint, breaks down why ransomware timelines are collapsing from weeks to hours, and walks through “half-click,” a Russian state-sponsored exploit that ran just from an email loading in a preview pane, no click required.

Dhawal Sharma, EVP of AI Security and Strategic Initiatives at Zscaler, explains why securing AI agents is a fundamentally different problem from securing human users, and why standard DLP policies miss an agent that’s doing something it was never intended to do.

Deepen Desai, Zscaler’s Chief Security Officer, shares results from Project Glass Wing, including a frontier model that bypassed its own security patch three times out of five, and makes the case for deception as the highest-value control against AI-driven attacks.

Todd Moore, Global VP and GM of data security products at Thales, explains why 2029 is closer than it sounds for quantum-safe cryptography, and what security leaders should be doing about it right now, not in three years.

The conversation covers why financial services, healthcare, and government are moving faster than retail and manufacturing, the emerging link between AI adoption and quantum risk, and the practical first step every security leader should take now: building a cryptographic inventory. Todd also introduces the concept of crypto agility. This is the ability to adapt as post-quantum algorithms and protocols continue to change, and unpacks Luna 8, Thales’ newly launched quantum-safe hardware security module, including why the company chose Black Hat to announce it.

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Pierson is a former CISO, chief privacy officer, and longtime Department of Homeland Security advisor who founded BlackCloak and created the digital executive protection category. He explains why the millions companies spend on cybersecurity rarely extend to the personal lives of their executives, and why that gap has become a material business risk, from data broker exposure and personal account breaches to home networks that can be compromised despite passing 41 straight weeks of penetration testing.

In this episode, they discuss:

• Why executives and their family members are targeted through data brokers, breached passwords and public profiles, and how that access can lead back into the company

• Real incidents BlackCloak has responded to, including a compromised home alarm and camera system and a virtual kidnapping scam built from social media activity

• How live, real-time deepfake voice and video attacks have outpaced Zoom and Teams-based verification, and why attackers simply call an executive’s personal device instead

• BlackCloak’s new circle of trust expansion, announced at Black Hat 2026, which extends out-of-band impersonation protection to trusted third parties like wealth advisors, attorneys and family staff

• Why digital executive protection has to operate outside the company, structured more like a health benefit than a corporate security function, to protect both executive privacy and the business

Olesen joined Cofense in January 2025, bringing over 30 years of technology leadership from roles including CEO at TokenEx, President and CEO at Sift, and senior leadership positions at Splunk and McAfee. He explains why polymorphic phishing, where AI generates a unique variation of an attack with every email, has become the default delivery model for attackers, and why AI has cut the time to build a phishing attack from 16 hours to five minutes.

In this episode, they discuss:

• Why 88% of AI-generated phishing attacks are now unique, and what that means for signature and rules-based defenses

• How business email compromise and OAuth/identity-based attacks still start with the inbox, even as phishing spreads to WhatsApp, Teams and other channels

• Cofense’s post-perimeter approach: combining AI-driven detection with human-verified intelligence to neutralize reported threats in under 10 minutes

• The “automation gap” between attacker and defender AI, and why a trained human layer will always be needed to close it

• What the next 12 months of phishing could look like, from deepfakes and voice cloning to new email confirmation workflows

• Olesen’s advice for security leaders building a defense-in-depth strategy against phishing

Up first is Deepen Desai, EVP and Chief Security Officer at Zscaler, who walks us through the ThreatLabz 2026 Phishing and Initial Access Report, highlighting the key trends that you need to be aware of.

That’s followed by Martyn Ditchburn, CTO in residence at Zscaler. He addresses the threat landscape from a European market perspective, looking at how phishing and AI-driven attacks are evolving and where organizations sit on the security maturity curve.

This is a public episode, if you’d like to discuss this with other subscribers or gain access to bonus episodes, visit podcasts.expertinsights.com

First, Swamy Kocherlakota, Executive Vice President, Agentic AI Startup at Zscaler, breaks down the AI security incidents enterprises are dealing with right now. He explains why zero trust is the right architectural response, and how AI coding tools are creating new attack vectors that security teams need to understand.

Then, Yaroslav Rosomakho, Chief Scientist at Zscaler, shares his perspective on agentic AI before moving into post-quantum cryptography: what the threat landscape looks like, and the practical steps organizations can start taking today.

In this episode, Expert Insights speaks with David Badanes, Human Risk Leader at Hoxhunt, about the findings from Hoxhunt’s 2026 Phishing Trends Report and what they mean for security teams trying to keep pace with AI-powered threats.
In this episode:

• Why AI has made high-quality phishing attacks accessible to any threat actor

• How phishing has expanded beyond email into calendars, SMS, and social platforms

• Why human-centric security training is now a business-critical investment

• How to spot AI-generated phishing emails before your users click

Recommended for CISOs, security awareness leads, and HR and risk leaders building a human-centered approach to cyber defense.

Sponsored by Hoxhunt.

In this episode, we share insights from 8 leaders at the conference, from the rise of shadow AI and autonomous agents to the reality that humans can’t keep up with machine-speed threats.

We explore how phishing is evolving, why agents are becoming a new insider risk, and how CISOs are being pushed to their limits as governance struggles to keep pace.

The big takeaway? Cybersecurity is becoming AI vs AI, and the organizations that put the right guardrails in place will come out ahead.

Key Timestamps:

• 00:49 - Everyone’s a developer now (The rise of AI agents)

• 01:22 – Shadow AI is already out of control

• 05:04 – The tipping point: AI vs AI security

• 09:25 – Phishing at machine speed

• 12:44 – The CISO breaking point (and what comes next)

• Why identity management is now the top attack vector

• How agentic AI can reduce alert fatigue and analyst burnout

• Why AI is becoming the new security perimeter

• How to rethink your SOC strategy with a platform-first approach

Recommended for CISOs, SOC leaders, and security analysts looking at AI-powered security operations.
Sponsored by Securonix

In this episode, Expert Insights speaks with Amber Britton, CEO of Doppler, about why secrets sprawl is one of the most underestimated risks in cybersecurity today.

In this episode:

• Why secrets sprawl is a growing and often overlooked security risk

• How AI agents are reshaping secrets management

• How to think about non-human identities in your security strategy

• Why developer experience is central to building a more secure organization

Recommended for CISOs, security engineers, and developers working on secrets management, cloud security, or AI-driven workflows.
Sponsored by Doppler

In this episode, we’ve included two of the interviews that Mirren conducted during the week. The first is from Scott Richards, SVP, AI & Discovery, and Cybersecurity, and the other from Muhi Majzoub, EVP of Cybersecurity Engineering at OpenText. The guests discuss the evolving nature of cybersecurity regulation, AI advances, and the steps that organizations need to take to protect themselves.

First with Netwrix, and now with Action1, Walters has a track record of building highly successful cybersecurity companies, laser focused on a specific niche.

What set Walters on this path?

It began with writing software. An early appreciation of scale and the realization that writing code alone couldn’t deliver impact fast enough pushed him and business partner Alex Vovk toward executing their own product vision.

From here, the pair launched Netwrix and Action1 into profitable, founder led businesses with no outside capital or investor pressure. Today, Netwrix is a multibillion-dollar organization with thousands of employees.

With Action1, Walters and Vovk are doing it again—but with even bigger ambition. They reinvested $20 million of their own capital to build a cloud-native platform engineered for the remote-work era. The bet has paid off. Action1 is now the fastest-growing private software company in America.

In this episode, Expert Insights’ Head of Content, Joel Witts, sits down with Mike Walters to explore his career and how patching is an often overlooked area of cybersecurity - as well as the parallels between building a company and surfing.

Host, Caitlin Harris, and Producer, Alex Zawalnyski, discuss insights from guests about work-life balance, the role of AI, compliance, and building a strong security culture, highlighting the unique perspectives women bring to the industry.

• (00:53) - Reflections on the Podcast Journey

• (03:05) - The Importance of Continuous Learning in Cybersecurity

• (05:40) - Diversity of Backgrounds in Cybersecurity

• (08:44) - Work-Life Balance and Avoiding Burnout

• (11:34) - Collaboration in Cybersecurity

• (14:42) - The Role of AI in Cybersecurity

• (17:29) - Compliance as a Springboard for Security Success

• (19:16) - Building a Strong Security Culture

Dana and Tia share decades of experience and industry accolades, offering actionable advice that any cybersecurity professional—or aspiring leader—can use to improve their career, team, and organization.

Listen now to hear from two of the top women shaping cybersecurity leadership today.

Inside this episode:

(01:20) - Introduction

(07:30) - The biggest challenges that modern CISOs are facing

(14:20) - How Agentic AI changes everything

(18:25) - The one thing that would make life easier

(26:30) - Fostering a culture of collaboration and accessibility

(32:55) - What does the future hold?

About Expert Insights

Expert Insights helps security and IT professionals make smarter, faster cybersecurity decisions. We cut through the noise with clear, free, and unbiased shortlists, guides, and expert articles, so you can find the right tools, faster.

Janine, Siroui, and Libby share decades of executive experience, offering practical insights for aspiring leaders, current executives, and anyone curious about the realities of running a tech organization.

Press play now to learn from the women shaping the future of cybersecurity from the top.

Inside this episode:

(01:20) - Introduction

(03:15) - The Role of Cybersecurity in boardroom decisions

(09:10) - Communication strategies for technical topics

(15:00) - The perception of women in the C-suite

(21:00) - Advice for people looking to forage a career in the C-suite

(28:20) - The CEO difference

(32:50) - Baking security into every decision

(40:45) - What sort of legacy do you want to leave?

About Expert Insights

Expert Insights helps security and IT professionals make smarter, faster cybersecurity decisions. We cut through the noise with clear, free, and unbiased shortlists, guides, and expert articles, so you can find the right tools, faster.

A: A culture that makes employees actually care about the security of their business.

And we’re not just talking about awareness training and password policies.

In this episode of Women In Cyber, host Caitlin Harris talks with Anne Cutler (Keeper Security), Molly McLain Sterling (Proofpoint), and Khush Kashyap (Vanta) about how you can cultivate a strong security mindset across your entire organization.

Anne, Molly, and Khush share decades of experience leading global cybersecurity strategy, education, and governance initiatives, offering practical advice and inspiration for anyone looking to strengthen their organization’s security culture.

Listen now to learn how these women are making security more human—and more effective.

Inside this episode:

(01:20) - Introduction

(02:50) - Strategies for creating an effective, organization-wide security culture

(08:00) - How to make security a shared responsibility

(13:10) - The role of employee training

(21:10) - Measuring success of culture changes

(30:20) - The importance of GRC in building a strategy

(36:45) - The place for empathy within cybersecurity

(39:00) - The changes that women are making today

About Expert Insights

Expert Insights helps security and IT professionals make smarter, faster cybersecurity decisions. We cut through the noise with clear, free, and unbiased shortlists, guides, and expert articles, so you can find the right tools, faster.

Nicole, Laura, and Emanuela bring decades of experience across threat intelligence, data strategy, and AI product innovation, offering insights and inspiration for anyone looking to innovate at the intersection of AI and cybersecurity.

Listen now to learn from the women shaping the future of AI in cyber.

Inside this episode:

(01:30) – Introduction

(06:50) - The rise of Agentic AI

(13:25) - The risks and rewards of deploying AI in the SOC

(17:50) - The cases where AI shouldn’t be used

(25:00) - How do you expect threat actors to harness AI?

(30:00) - How women in cyber becomes a way of life

(33:20) - Developing AI for technical and non-technical users

(36:10) - Advice for breaking into the Cyber AI space

About Expert Insights

Expert Insights helps security and IT professionals make smarter, faster cybersecurity decisions. We cut through the noise with clear, free, and unbiased shortlists, guides, and expert articles, so you can find the right tools, faster.

Sezaneh and Courtney share decades of experience at the intersection of policy, risk management, and national security, providing actionable insights for anyone looking to understand or influence the evolving regulatory landscape.

Play now to hear from the women shaping the rules of cybersecurity.

Inside this episode:

(01:30) - Introduction

(4:50) - Proactive cybersecurity risk management

(08:55) - Understanding cybersecurity insurance misconceptions

(13:50) - Quantifying risk in an evolving landscape

(18:00) - The geopolitical risks of cybersecurity policies

(25:00) - The accessibility of cybersecurity resources

(29:15) - Aligning security with business goals

About Expert Insights

Expert Insights helps security and IT professionals make smarter, faster cybersecurity decisions. We cut through the noise with clear, free, and unbiased shortlists, guides, and expert articles, so you can find the right tools, faster.

Margaret, Kavita, and April share their experiences leading product strategy, developing enterprise solutions, and combining technical expertise with user-focused design—offering actionable insights for anyone working at the intersection of cybersecurity, technology, and innovation.

Listen now to learn how these women are shaping the next generation of cybersecurity products.

Inside this episode:

(01:30) - Introduction

(06:20) - Balancing innovation with governance in security products

(13:00) - The role of user feedback in shaping impactful solutions

(19:20) - The role of Agentic AI in the future of cybersecurity

(27:40) - The intersection between cybersecurity and national security policy

(37:40) - How can you build trust with new security tools

About Expert Insights

Expert Insights helps security and IT professionals make smarter, faster cybersecurity decisions. We cut through the noise with clear, free, and unbiased shortlists, guides, and expert articles, so you can find the right tools, faster.