A podcast about the IT and security leaders rewriting the rules. Not just patching what's broken, but building what's next. In every episode, we explore how modern teams are replacing outdated ways of working with simpler, smarter, and more strategic approaches.
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Balancing Security with Speed with Ralph Pyne, CISO, Apollo.io
Host Alex Stamos interviews Ralph Pyne, CISO of Apollo.io, about embracing AI and citizen developers by assuming security failure and adopting statistical models.
20 May 2026TRANSCRIPT
Why More Security Tools = Less Security with Jonathan Poon, Head of Threat & Vulnerability Management at Zoom
Jonathan Poon, Head of Threat & Vulnerability Management at Zoom, explains how too many security tools can decrease security and offers strategies for streamlining your security stack.
17 Sept 2025TRANSCRIPT
RBAC is Broken (Here's Why) with Dmitri Altum, GitLab, ex-Ramp
In this episode of Patch Me If You Can™, Arek Dreyer sits down with Dmitri Altum, Staff Security Engineer at GitLab, who breaks down why Role Based Access Control (RBAC) is failing modern businesses.
Dmitri shares his experience building dynamic identity systems that analyze user behavior rather than relying on static job titles, especially as AI blurs traditional role boundaries. He also demonstrates how his team achieved 93% automated approval rates with just 3 second response times, proving that security and speed don't have to pull in opposite directions.
20 Aug 2025
Standard Users in an Admin World with Collin Elliott, Capital One
In this episode of Patch Me If You Can™, Arek Dreyer sits down with Collin Elliott, Senior Platform Engineer at Capital One, to unpack the challenges of balancing strong security with a smooth user experience in endpoint management.
They explore topics such as the shift to least privilege, the tools and strategies that help, and why leadership buy-in and thoughtful automations are keys to success.
6 Aug 2025
Why 99% Hit Defer Every Time with Robert Hammen, SAP, ex-SpaceX
In this episode of Patch Me If You Can™, Arek Dreyer sits down with Robert Hammen, Principal Mac Consultant at SAP and former IT Systems Engineer at SpaceX, to dig into various topics, including the world of enterprise patch management.
They dig into the complexities and opportunities of patch management at scale. The big question: Why does patching still feel so painful, and what strategies actually drive better compliance and security without alienating end users?
23 Jul 2025
Mac Malware: The Cat & Mouse Game with Patrick Wardle
In this episode of Patch Me If You Can™, Arek Dreyer sits down with Patrick Wardle, a leading figure in macOS security.
Patrick, who founded the Objective-See Foundation and the Objective by the Sea security conference, brings years of frontline experience from organizations like NASA and the NSA. He’s also the author of the Art of Mac Malware book series and has created several widely used open-source macOS security tools, giving him a unique perspective on both defending and attacking modern Mac systems.
9 Jul 2025
AI Driven IT: Less Toil, More Impact with Emanuele Sparvoli, Director of IT at Intercom
In this episode of Patch Me If You Can™, Arek Dreyer welcomes Emanuele Sparvoli, the Director of IT at Intercom, to discuss key challenges and solutions facing modern IT teams.
At Intercom, Emanuele has driven a cultural and technical shift to treat IT not simply as a support function, but as a strategic driver, focusing on designing systems that are secure, automated, intuitive, and built around the needs of users.
In this episode, Emanuele discusses the complexities of securing non-human service accounts—like bots and automated systems—the shortcomings of industry-standard security approaches, and how Intercom addressed these pain points.
Emanuele dives into how automation and AI are freeing IT professionals to spend less time on repetitive tasks and more time improving systems and processes. As a result, his team boosts efficiency, reduces toil for both IT and users, and helps the company scale securely. Tune in for insights on how to do the same in your organization.
25 Jun 2025
Service Accounts Gone Wild with Kane Narraway, Head of Enterprise Security at Canva | Patch Me If You Can™
In this episode of Patch Me If You Can™, Arek Dreyer chats with Kane Narraway, Head of Enterprise Security at Canva, about the toughest challenges in modern security.
From Zero Trust for non-human identities to secure AI adoption, Kane draws on his experience at places such as Shopify, Atlassian, and the UK government to share actionable strategies and career insights.
11 Jun 2025
People, Process, Tech with Eric Pittman, VP of Cybersecurity at Teradata
In this episode of Patch Me If You Can™, Arek Dreyer sits down with Eric Pittman, the Vice President of Cybersecurity at Teradata, to discuss the evolving world of cybersecurity and vulnerability management.
Eric brings a wealth of experience from years on the cybersecurity frontlines, including leading teams through critical incidents like major ransomware attacks and collaborating with agencies such as the FBI.
Throughout this episode, Eric emphasizes the importance of a holistic, people-first approach to security, built on the pillars of people, process, technology, and business value. He highlights strategies such as conducting awareness campaigns, tailoring patching processes to different user groups, and automating routine tasks to reduce human error and accelerate response times, all while sharing practical lessons learned.
4 Jun 2025
The Problem No One Patches with Aaron Morin, ex-Nike
In this episode of Patch Me If You Can™, Arek Dreyer welcomes Aaron Morin, currently the GM of Platform at Kandji and formerly the lead mobility engineer at Nike.
Aaron’s diverse experience—both in hands-on IT engineering at a global corporation and at the strategic leadership table—sets the stage for a candid discussion about modern IT challenges and opportunities. His background gives him a unique perspective on how technical teams collaborate, adapt, and innovate in organizations where the complexity of systems can be overwhelming.
This episode dives into IT leadership, BYOD challenges, cross-functional teamwork, and how smart communication and data use drive modern IT success.
28 May 2025
Balancing Security vs. User Experience with Richard Hiralal, Grammarly
In this episode of Patch Me If You Can™, Arek Dreyer welcomes Richard Hiralal, Systems Engineer at Grammarly, for a revealing conversation about the realities of maintaining secure systems without sacrificing user experience. Richard not only understands the technical demands of endpoint security but also has a keen sense for how organizational friction arises between users, IT, and security teams. Richard’s background in keeping critical systems protected while ensuring productivity sets the stage for an exploration of what it takes to design and uphold modern, user-friendly security practices.
Inside a recent episode
Balancing Security with Speed with Ralph Pyne, CISO, Apollo.io
Published 17 Jun 2026 · Transcript excerpt
[…] There's so much more to consider around like data classification and privilege. And like you mentioned, the information that's training the model. How do you ring fence that? I think that's going to be a challenge that many companies have to deal with in moving into this AI era. I think the other thing is you also have to assume failure. I think we come from a principle in security of there's a set of binary decisions and if we do enough work, we can make things secure. I'm not saying that's real because it's not, but I think there's almost been... Again, why the principle is privilege is irritating to me because there's this assumption of, oh, you do the right set of things and it's going to be okay. […]
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