The Human Side of Cybersecurity

In this episode of the Human Side of Cybersecurity, Dan Desko, Founder & CEO of Echelon Risk + Cyber, speaks with Dr. Trebor Evans, SVP and CISO at Dollar Bank, about leadership, pressure, and maintaining perspective in one of the most demanding roles in the industry. Leading security at a 170-year-old financial institution, Trebor shares how experience, judgment, and self-awareness shape effective decision-making over time. The discussion moves beyond tools and frameworks into how leaders manage urgency, assess real impact, and show up calmly when others are under stress. Trebor reflects risk, anxiety, mentorship, and why not every issue deserves a full-scale reaction. For current and aspiring security leaders, this conversation offers a grounded look at what it takes to sustain leadership and credibility over the long run. Leave us a review wherever you get your podcasts!

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In this episode of the Human Side of Cybersecurity, Dan Desko, Founder & CEO of Echelon Risk + Cyber, speaks with Julie Ray, VP and CISO at Wabtec Corporation, about building an effective security leadership style over time. Drawing on a career that spans infrastructure, compliance, and manufacturing, Julie shares how her perspective on cybersecurity has evolved, moving beyond tools to focus on governance, communication, and judgment. The conversation explores why clear, concise communication is one of the most critical skills for CISOs, how mentorship and community shape long-term success, and why continuous learning matters in a role defined by constant change. For both current and aspiring security leaders, Julie offers practical insight into what it takes to lead with credibility in complex organizations. Leave us a review wherever you get your podcasts!

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In this episode of The Human Side of Cybersecurity, Dan Desko, Founder & CEO of Echelon Risk + Cyber, sits down with Margarita Rivera, Global CISO at Carnival Corporation, to explore an unconventional path into cybersecurity leadership. Margarita shares how her career began in business and risk management, evolved through mentorship and persistence, and ultimately led her to securing one of the most complex environments in the world. The discussion covers leadership growth, the value of mentorship, and what it means to protect a global organization made up of multiple brands operating as “floating cities.” For current and aspiring security leaders, this conversation offers a grounded look at how curiosity, commitment, and adaptability shape long-term success in the role.

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In this episode of The Human Side of Cybersecurity, Dan Desko, Founder & CEO of Echelon Risk + Cyber, sits down with Paul Guerra, CISO at Rackspace Technology, to discuss what security leadership really looks like inside fast-moving organizations. Paul shares how building and fixing security programs during moments of change shaped his view of the role, not as a technical function, but as a discipline rooted in trust, communication, and business outcomes. The discussion explores why the CISO role is often a sales role, how leaders earn executive alignment, and why talent alone is never enough without discipline and follow-through. Paul also reflects on mentorship, teamwork, and the importance of doing the hard work when it matters most. Leave us a review wherever you get your podcasts!

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In this episode of The Human Side of Cybersecurity, Dan Desko, Founder & CEO of Echelon Risk + Cyber, sits down with John Scrimsher, CISO at Kontoor Brands, to explore how security leadership evolves over decades of change. John reflects on a career that began before modern security programs existed, shaped by early malware outbreaks, large-scale incidents, and the need to innovate when tools didn’t yet scale. The discussion focuses on how experience, adaptability, and community shape long-term effectiveness in the role. The conversation moves beyond technology into leadership, communication, and resilience. John shares lessons learned from professional missteps, cultural adaptation, and managing pressure over time, while also challenging misconceptions about what senior security leadership actually entails. For current and aspiring leaders, the discussion offers a grounded perspective on why security is as much about people, trust, and persistence as it is about controls.

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In this episode of The Human Side of Cybersecurity, Dan Desko, Founder & CEO of Echelon Risk + Cyber, sits down with Michael South, CISO at Dick’s Sporting Goods, for a candid discussion about leadership, pressure, and how the role changes over time. Drawing on nearly three decades of experience across the Navy, IT, operations, government, and retail, Michael shares how his perspective on risk has been shaped less by technology and more by operational reality, human impact, and business context. The conversation moves beyond tools to examine what sustained urgency does to people and judgment. Michael reflects on learning the hard way, particularly during early cloud adoption, why restraint, empathy, and prioritization matter as much as technical expertise. He also addresses burnout as an operational risk, explaining why leaders must be intentional about protecting teams from unnecessary pressure. The discussion offers a grounded look at what it actually takes to lead security programs at scale.

In this episode of The Human Side of Cybersecurity, Dan Desko, Founder & CEO of Echelon Risk + Cyber, speaks with Dom Glavach of CyberSN about what security leadership looks like once the responsibility extends beyond systems and into people. Dom reflects on a career that began deep in the technical work, long before many modern security roles were formalized, and how that foundation continues to shape how he views risk, leadership, and accountability. The discussion centers on Dom’s belief that cybersecurity is ultimately a human problem, not a technical one. He shares a defining incident where unclear communication during a response led to unintended escalation, reinforcing how fatigue and pressure expose leadership gaps faster than tooling ever will. The conversation also challenges the industry’s tendency to chase headline threats without fully understanding the environment, including how organizations approach AI risk today. For current and aspiring leaders, Dom offers a grounded perspective: invest in people, treat communication as a core security skill, and recognize that leadership in security is a long game shaped by judgment under pressure.

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In this episode of The Human Side of Cybersecurity, Dan Desko, Founder & CEO of Echelon Risk + Cyber, speaks with Aaron Stanley, Head of Security at DBT Labs, about what the security role becomes once the focus shifts away from tooling and toward long-term leadership. Aaron reflects on a career shaped less by titles and more by persistent questions around privacy, trust, and accountability—an outlook that frames security as an ongoing responsibility rather than a discrete function. The discussion explores formative leadership moments that reshaped how Aaron builds teams, including a hard lesson learned when an application security organization faltered after leaning too heavily into an engineering-first model. The conversation also challenges familiar enterprise security patterns, from the real return on phishing simulations to overly granular access controls, and reframes burnout as a leadership signal tied to disengagement and lack of visible impact. For those earlier in their careers, Aaron offers a grounded perspective on the role itself: meaningful progress in security comes from influencing people, shaping culture, and playing the long game.

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In this episode of The Human Side of Cybersecurity, Dan Desko, Founder & CEO of Echelon Risk + Cyber, sits down with Bob Kemp, Global CISO at Federated Hermes, to discuss how credibility is built and sustained in the security leadership role. Bob reflects on a career path that began in accounting and finance, moved through IT and customer-facing roles, and ultimately led to security leadership, an experience that deeply shapes how he thinks about risk, communication, and accountability inside complex organizations. The conversation moves quickly beyond titles and tools. Bob shares how his leadership style evolved as expectations and organizational complexity increased, including a formative moment early in his tenure when an executive update turned into an extended interrogation that forced him to rethink how security decisions were framed. He also challenges common industry habits, from chasing hype to over-investing in activities with limited return, and emphasizes grounding security conversations in fundamentals and business context. For those earlier in their careers, Bob offers a clear reframing of the role: risk belongs to the business, and the CISO’s job is to surface it clearly, communicate tradeoffs honestly, and build trust over time.

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In this episode of The Human Side of Cybersecurity, Dan Desko, Founder & CEO of Echelon Risk + Cyber, sits down with John O’Rourke, CISO at PPG Industries, to discuss how the security role evolves inside a large, globally distributed manufacturing organization. Drawing on his 18-year career at PPG, John reflects on his transition from software development and M&A integration into security leadership, and how that path shaped his views on risk, governance, and accountability. The conversation moves beyond tools to the realities of leadership at scale. John shares how his approach changed as threats accelerated, stepping back from day-to-day technical decisions to focus on building strong teams, establishing trust-based operating models, and remaining accountable for outcomes. He also challenges common assumptions in enterprise security, including the limited return many organizations see from third-party risk questionnaires, and explains why governance quality, process rigor, and clear executive communication often matter more than additional tooling.Leave us a review wherever you get your podcasts!

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