In this episode, I speak with three guests from diverse backgrounds who share a common goal: Building trust in human-AI partnerships in security. We originally came together for a panel at the Institute of Electrical and Electronics Engineers (IEEE) Conference on AI in May 2025, and this episode recaps that discussion.

Key takeaways:

• Security practitioners tend to be natural-born skeptics (can you blame them?!). They struggle to trust and adopt AI-powered security products, especially in higher-risk scenarios with overly simplified decision-making processes.
• AI can be a tool for threat actors and a threat vector itself, and its non-deterministic nature makes it unpredictable and vulnerable to manipulation.
• All AI models are biased, but not all bias is negative. Recognized and carefully managed bias can provide actionable insights. Purposefully biased (opinionated) models should be transparent.
• Clearer standards and expectations are needed for “human-in-the-loop” and human oversight. What does the human actually do, are they qualified, and do they have the right experience and information?
• What happens when today’s graduates are tomorrow’s security practitioners? On one end of the spectrum we have a lot of skepticism, on the other end not enough. We talk about over-reliance on AI, de-skilling, and loss of situational awareness.

Dr. Margaret Cunningham is the Technical Director, Security & AI Strategy at Darktrace. Margaret was formerly Principal Product Manager at Forcepoint and Senior Staff Behavioral Engineer at Robinhood.

Dr. Divya Ramjee is an Assistant Professor at Rochester Institute of Technology (RIT). She also leads RIT’s Technology and Policy Lab, analyzing security, AI policy, and privacy challenges. She previously held senior roles in US government across various agencies.

Dr. Matthew Canham is the Executive Director, Cognitive Security Institute. He is a former FBI Supervisory Special Agent, with over twenty years of research in cognitive security.

You're a founder with a great cybersecurity product—but no one knows or cares. Or you're a marketer drowning in jargon (hey, customers hate acronyms, too), trying to figure out what works and what doesn’t. Gianna Whitver, co-founder of the Cybersecurity Marketing Society, breaks down what the cybersecurity industry is getting wrong—and right—about marketing.

In this episode, we talk about:

• Cyber marketing is hard (but you knew that already). It requires deep product knowledge, empathy for stressed buyers, and clear, no-FUD messaging.
• Building authentic, value-driven communities leads to stronger cybersecurity marketing impact.
• Don’t copy the marketing strategies of big enterprises. Instead, focus on clarity, founder stories, and product-market fit.
• Founder-led marketing works. Early-stage founders can break through noise by sharing personal stories.
• Think twice before listening to the advice of “influencer” marketers. This advice is often overly generic. Or, you’re following advice of marketers marketing to marketers (try saying that ten times fast). In other words, their advice is probably not going to apply to cybersecurity.

Gianna Whitver is the co-founder and CEO of the Cybersecurity Marketing Society, a community for marketers in cybersecurity to connect and share insights. She is also the podcast co-host of Breaking Through in Cybersecurity Marketing podcast, and founder of LeaseHoney, a place for beekeepers to find land.

Users, threat actors, and the system design all influence—and are influenced by—one another. To design safer systems, we first need to understand the players who operate within those systems. Kelly Shortridge and Josiah Dykstra exemplify this human-centered approach in their work. In this episode we talk about:

• The vital role of human factors in cyber-resilience—how Josiah and Kelly apply a behavioral-economics mindset every day to design safer, more adaptable systems.
• Key cognitive biases that undermine incident response (like action bias and opportunity costs) and simple heuristics to counter them.
• The “sludge” strategy: deliberately introducing friction to attacker workflows to increase time, effort, and financial costs—as Kelly says, “disrupt their economics.”
• Why moving from a security culture of shame and blame to one of open learning and continuous improvement is essential for true cybersecurity resilience.

Kelly Shortridge is VP, Security Products at Fastly, formerly VP of Product Management and Product Strategy at Capsule8. She is the author of Security Chaos Engineering: Sustaining Resilience in Software and Systems.

Josiah Dykstra is the owner of Designer Security, human-centered security advocate, cybersecurity researcher, and former Director of Strategic Initiatives at Trail of Bits. He also worked at the NSA as Technical Director, Critical Networks and Systems. Josiah is the author of Cybersecurity Myths and Misconceptions: Avoiding the Hazards and Pitfalls that Derail Us.

During this episode, we reference:

Josiah Dykstra, Kelly Shortridge, Jamie Met, Douglas Hough, “Sludge for Good: Slowing and Imposing Costs on Cyber Attackers,” arXiv preprint arXiv:2211.16626 (2022).

Josiah Dykstra, Kelly Shortridge, Jamie Met, Douglas Hough, “Opportunity Cost of Action Bias in Cybersecurity Incident Response,” Proceedings of the Human Factors and Ergonomics Society Annual Meeting, 66, Issue 1 (2022): 1116-1120.

Imagine a world where product teams collaborate with security teams. Where product designers can shadow their security peers. A place where security team members believe communication is one of the most important skillsets they have. These are key attributes of human-centered security—the type of dynamics Jordan Girman and Mike Kosak are fostering at Lastpass.

In this episode, we talk about:

• What cross-disciplinary collaboration looks like at Lastpass (for example, a product designer is shadowing the security team).
• A set of principles for designing for usable security and privacy.
• Why intentional friction might be counterintuitive to designers but, used carefully, is critical to designing for security.
• When it comes to improving security outcomes, the words you use matter. Mike explains how the Lastpass Threat Intelligence team thinks about communicating what they learn to a variety of audiences.
• How to build a threat intelligence program within your organization--even if you have limited resources.

Jordan Girman is the VP of User Experience at Lastpass. Mike Kosak is the Senior Principal Intelligence Analyst at Lastpass. Mike references a series of articles he wrote, including “Setting Up a Threat Intelligence Program From Scratch.” 

Where are security tools failing security teams? What are security teams looking for when they visit a security vendor marketing website? Paul Robinson, security expert and founder of Tempus Network, says, “Over-promising and under-delivering is a major factor in these tools. The tool can look great in a demo—proof of concepts are great, but often the security vendor is just putting their best foot forward. It's not really the reality of the situation.”

Paul’s advice for how can security vendors do better? 

• Start by admitting security isn’t just a switch you flip—it’s a journey. 
• Security teams aren’t fooled by glitz and glamour on your marketing website. They want to see how you addressed real problems.
• Incredible customer service can make a small, scrappy cybersecurity product stand out from larger, slower-moving vendors.
• Cybersecurity vendors need to get onboarding right (it’s a make or break aspect of the user experience). There are more variables than you think—not only technology but also getting buy-in from employees, leadership, and other stakeholders.
• Think about the user experience not only of the person using the security product, but the people at the organization who will be impacted by the product.

Looking for a cybersecurity-related movie that is just a tad too plausible? Paul recommends Leave the World Behind on Netflix.

When we collaborate with people, we build trust over time. In many ways, this relationship building is similar to how we work with tools that leverage AI. 

As usable security and privacy researcher Neele Roch found, “on the one hand, when you ask the [security] experts directly, they are very rational and they explain that AI is a tool. AI is based on algorithms and it's mathematical. And while that is true, when you ask them about how they're building trust or how they're granting autonomy and how that changes over time, they have this really strong anthropomorphization of AI. They describe the trust building relationship as if it were, for example, a new employee.” 

Neele is a doctoral student at the Professorship for Security, Privacy and Society at ETH Zurich. Neele (and co-authors Hannah Sievers, Lorin Schöni, and Verena Zimmermann) recently published a paper, “Navigating Autonomy: Unveiling Security Experts’ Perspective on Augmented Intelligence and Cybersecurity,” presented at the 2024 Symposium on Usable Privacy and Security. 

In this episode, we talk to Neele about:

• How security experts’ risk–benefit assessments drive the level of AI autonomy they’re comfortable with.
• How experts initially view AI: the tension between AI-as-tool vs. AI-as-“teammate.”
• The importance of recalibrating trust after AI errors—and how good system design can help users recover from errors without losing their trust in it.
• Ensuring AI-driven cybersecurity tools provide just the right amount of transparency and control.
• Why enabling security practitioners to identify, correct, and learn from AI errors is critical for sustained engagement.

Roch, Neele, Hannah Sievers, Lorin Schöni, and Verena Zimmermann. "Navigating Autonomy: Unveiling Security Experts' Perspectives on Augmented Intelligence in Cybersecurity." In Twentieth Symposium on Usable Privacy and Security (SOUPS 2024), pp. 41-60. 2024.

In this episode, Heidi gets a taste of her own medicine and is interviewed by co-host John Robertson about her newly-released book Human-Centered Security: How to Design Systems That Are Both Safe and Usable. We talk about:

• Why Heidi’s experience as a UX researcher prompted her to write Human-Centered Security.
• Places in the user journey where security impacts users the most.
• Why cross-disciplinary collaboration is important—find your security UX allies (people in security, legal, privacy, engineering, product managers, to name a few).
• Practical security UX tips like secure by default, guiding the user along the safe path, and being really careful about the words you use.
• Technical users—IT admins, engineers, security analysts—are users, too and why it’s so important to thoughtfully design the security user experience for them. (Spoiler: they help keep the rest of us safe!)

The cybersecurity industry often fixates on “behavior change,” expecting users to take on unrealistic tasks instead of designing safer, smarter systems. 

Matt Wallaert (founder of BeSci.io and author of Start at the End: How to Build Products that Create Change) explains behavioral science isn't about forcing behavior change. Instead, it's about understanding people so a thoughtfully-designed system can influence more secure outcomes.

Whether you’re a UX designer, a security engineer, or a CISO, you influence security behaviors. Here’s how you can move towards more secure outcomes:

• Stay Ahead of Threat Actors: Cybercriminals use behavioral science to their advantage. People designing the security user experience must not only catch up but outpace them.
• Define Clear Outcomes: Don’t just say “we want users to be secure.” Know exactly what behaviors you want and why. Vague goals lead to vague results.(as Matt explains, saying things like “I want people to be more secure” isn’t helpful. In fact, many people don’t know what “more secure” means in the context of their product or organization).
• Ask Better Questions: Use tools like the “sufficiency test.” For example, sure, it might be nice if users created complex passwords—but users don’t necessarily have to be the ones doing it. Why can’t the system create a complex password for them (as password managers do)?
• Understand promoting and inhibiting pressures. These concepts will help you design systems that are more resilient because they are built with people in mind. There are reasons people do and do not do things—when you understand why, you can develop systems that will be more effective in encouraging the behaviors you want. 
• Security practitioners: tired of being perceived as the “department of no”? Matt explains how behavioral science can help you better collaborate with cross-disciplinary teams.

Bonus: UX designers, after this episode you may never create another persona.

“Technical people need to better understand the laws and regulations and lawyers need to better understand the technology and processes in place. When that happens, when those worlds come together, that’s where you can meaningfully make things happen.” -Justine Phillips, Partner at Baker McKenzie

In this episode, we talk about:

• Essential questions product teams should ask legal experts when integrating AI into new products and features.
• In particular, why it’s important for designers and engineers to question the source of the data they are using for AI-powered products and features.
• The need to anticipate international security and privacy regulations, which are constantly changing, including emerging regulations that could impact companies developing IoT devices.

Justine Phillips is a Partner at Baker McKenzie, where she is co-chair of data+cyber for the Americas. She is the author of Data Privacy Program Guide: How to Build a Privacy Program That Inspires Trust.

What do CISOs have to say about the security tools their teams use?:

In this episode, we talk to cybsecurity leaders Bill Bonney, Gary Hayslip, and Matt Stamper about:

• The ever-evolving role of the CISO and what CISOs care about most.
• What product teams designing security software need to understand:
  • Security tools need to operate across varied ecosystems (which means your product team needs to understand those ecosystems).
  • Complexity is the enemy of security. Yes, UX matters.
  • Context-switching means security teams waste time. Instead, security tools need to present the right information at the right time.
  • Why CISOs are excited to leverage AI in security tools—and what concerns them the most.

Bill Bonney, Gary Hayslip, and Matt Stamper are seasoned CISOs and cybersecurity leaders. They are co-founders of the CISO Desk Reference Guide—a series of books including topics such as security policy, third-party risk, privacy, and incident response—which provide actionable insights for security leaders.