Bryan Tomczyk serves as a Cybersecurity Engineer at GP Strategies Corporation, where he works closely with senior IT and infrastructure teams to secure systems across a large, global organization. GP Strategies operates primarily as a training and professional services company, supporting clients across multiple countries and industries. Bryan's role places him at the intersection of security engineering, vendor risk management, and user education, with a strong emphasis on enabling the business rather than obstructing it. His background reflects a long term evolution into cybersecurity, shaped by decades of security focused thinking before formally entering a cyber role.

• Why cybersecurity must be embedded into every role, not isolated to IT teams

• How security advocacy grows organically through education and experience

• The real risks of AI adoption without proper guardrails

• Why large language models are not a complete solution for security

• How supply chain risk has become one of the biggest threats to organizations

• What secure by design actually looks like in modern environments

• Practical considerations for evaluating AI tools and SaaS vendors

Bryan Tomczyk explains why the idea that security is everyone's job only works when organizations invest in education and context. He describes how working directly with users, especially after incidents, creates awareness that policies alone cannot achieve. Security, in his view, must enable productivity while quietly reducing risk in the background.

The conversation dives deep into AI and cybersecurity, with Bryan outlining why machine learning excels at correlating massive volumes of data but struggles when used without constraints. He cautions against treating large language models as universal solutions, noting their susceptibility to hallucination, prompt injection, and misuse. Instead, he advocates for narrowly scoped, self learning systems that are heavily restricted in access.

Bryan also addresses the growing complexity of modern environments, from email security and MFA fatigue to operational technology and supply chain risk. He highlights why vendor reviews, SOC 2 reports, and infrastructure transparency are no longer optional. Throughout the discussion, he reinforces a consistent theme that security must evolve thoughtfully, balancing innovation with responsibility to protect users, data, and operations.

Zach Lewis serves as both CIO and CISO at the University of Health Sciences and Pharmacy in St. Louis, bringing nearly a decade of experience across engineering, systems administration, help desk leadership, and executive IT leadership. He oversees technology operations and cybersecurity for one of the oldest pharmacy institutions in the United States, balancing academic continuity, research integrity, and institutional resilience. Zach is also the author of the upcoming book Locked Up: Cybersecurity Threat Mitigation, Lessons from a Real World LockBit Ransomware Response, which documents a firsthand ransomware incident and the leadership decisions required to navigate it. His perspective blends technical depth with lived experience under real pressure.

• What actually happens inside an organization during a LockBit ransomware attack

• Why incident response planning looks very different in practice than on paper

• How leadership stress, decision making, and communication shape outcomes

• Why recovery and resilience matter more than the illusion of prevention

• How tabletop exercises help but still fail to predict real world chaos

• What CISOs should expect emotionally, operationally, and politically during an incident

• Why transparency and shared learning are still rare but critically needed

• How post incident investments and tooling decisions should be evaluated

Zach Lewis walks through the ransomware incident that ultimately inspired his book. The attack began with system outages that initially looked like aging infrastructure failures during a period of delayed hardware refreshes caused by supply chain issues. After briefly restoring systems, the environment collapsed again, revealing a ransomware note at the hypervisor level. By that point, core files had been encrypted, leaving little opportunity for traditional endpoint or EDR controls to intervene.

Zach explains the rapid shift from disaster recovery to full incident response. External forensics teams, negotiators, cyber insurance, legal counsel, and federal authorities were brought in while the university worked to remain operational. Thanks to a SaaS first strategy adopted prior to the incident, students and faculty were largely unaffected, even as backend systems were rebuilt. Full recovery and remediation took nearly two months, with teams working long hours under extreme pressure.

A central theme of the conversation is the human side of ransomware. Zach describes the stress placed on leadership, the emotional toll on staff, and the importance of remaining calm when others are overwhelmed. He emphasizes that CISOs are not hired to prevent every incident, but to respond, recover, and lead through uncertainty. Clear communication with executives, boards, and end users became just as important as technical recovery.

Zach also discusses why he chose to write Locked Up. Ransomware incidents are often hidden due to legal and reputational concerns, leaving practitioners without real guidance. By openly documenting what happened, including mistakes and lessons learned, Zach aims to provide a practical framework for others who will inevitably face similar events. He closes with advice on incident response planning, out of band communication, backup testing, password manager access, and the value of pre established relationships with the FBI and CISA.

Guest Introduction

Andrew DeBratto, Chief Information Security Officer at Hunton Andrews Kurth LLP, leads cybersecurity strategy for one of the world's top 100 law firms. With more than 25 years in IT and two decades in the legal sector, Andrew combines operational discipline with forward-thinking innovation. His leadership at Hunton Andrews Kurth emphasizes cybersecurity as both a client obligation and a business enabler. Guiding a global IT team of more than 90 professionals, he champions "operational excellence" as the foundation for secure innovation. His practical insights reveal how large legal organizations can maintain stability while exploring emerging technologies like AI, automation, and micro-segmentation.

Here's a Glimpse of What You'll Learn:

• Why operational excellence is the foundation of every successful IT department
• How Hunton Andrews Kurth builds trust through proactive cybersecurity practices
• The role of ethical AI use in the legal industry
• Why attitude and aptitude outweigh certifications in IT hiring
• How the firm applies micro-segmentation and zero trust principles effectively
• Why lawyers must remain human-in-the-loop when using AI tools
• How innovation and practicality coexist in modern law firms

In This Episode:

Andrew DeBratto shares an inside look at how Hunton Andrews Kurth balances cybersecurity, innovation, and productivity across its global operations. He explains that "keeping the lights on" through operational excellence creates the foundation for innovation. When systems run smoothly and attorneys can focus on their clients, IT earns the credibility to explore transformative projects like AI integration and advanced endpoint protection.

Andrew dives into the realities of cybersecurity in the legal sector, where firms are prime targets for sophisticated threat actors. Hunton Andrews Kurth conducts regular penetration tests and tabletop exercises not for compliance, but for genuine improvement. "Find the flaws," Andrew insists, emphasizing that vulnerability detection drives resilience. His team uses a best-of-breed approach, prioritizing specialized tools that deliver depth of security over one-size-fits-all platforms.

The discussion also explores AI's growing influence on legal practice. Andrew acknowledges its potential but insists that every AI implementation at the firm is bound by responsible-use training. Attorneys must complete ethical certification before using any generative AI platform. "You are still responsible for your work," he reminds listeners, underscoring that human judgment must remain central even as technology accelerates productivity.

Later in the conversation, Andrew highlights the firm's AI strategy, which blends internal development on Microsoft Azure OpenAI with external best-of-breed tools. Rather than chasing every new platform, the firm uses a "buffet approach," allowing experimentation without overspending. AI, he notes, is still in its exploratory phase, and meaningful productivity gains will come only when the right tools align with specific workflows.

On leadership, Andrew emphasizes hiring for attitude and aptitude. Technical skills can be taught, but curiosity, collaboration, and integrity are essential. His philosophy has built a team that is both technically capable and deeply aligned with the firm's mission of trust, innovation, and client service.

Rao Tadepalli is the CEO and Founder of DigiTran, a digital transformation and AI advisory firm specializing in insurance and financial services. Previously the CIO of Slide Insurance, Rao has spent decades guiding insurers through modernization, core system evolution, cloud adoption, and AI driven process redesign. Today he helps carriers, agents, and insuretechs move from legacy workflows to a forward looking operating model that blends automation, human expertise, and strong governance. His background gives him a rare perspective that combines deep technical knowledge, board level thinking, and a practical grasp of the challenges faced by regulated industries.

• How AI accelerates claims processing for insurers while preserving the human in the loop for complex cases

• Why AI is creating new job categories such as prompt engineering instead of simply eliminating roles

• How DigiTran guides carriers through digital transformation and modernization of core systems

• Why financial services require both safety mindset and compliance mindset at the leadership level

• How AI powered security tools reshape detection and response in a high threat environment

• Why layered security, policies, procedures, and end user training must work together

• How leadership perception of IT needs to shift from cost center to value creation team

• Why communication, visibility, and proactive reporting help CIOs gain influence across the business

Rao opens by explaining DigiTran's mission: helping insurance organizations evolve from legacy systems into modern, AI supported operating environments. He outlines why insurance is uniquely sensitive to modernization cycles given the regulatory landscape, the importance of claims accuracy, and the constant need for faster service for policyholders. Rao describes how AI shines in straightforward claims workflows, especially situations where outcomes are predictable and repeatable. At the same time, he emphasizes that high complexity claims still demand human involvement, empathy, and judgment.

The conversation shifts to workforce evolution. Rao details how AI does not eliminate people, but pushes organizations to retrain and rethink skill development. He explains why prompt engineering is becoming a necessary capability for future professionals and shares how he created a promptathon that taught students how to approach prompts systematically. His lesson is simple and powerful: as technology changes, the workforce must adapt in ways that preserve value, not shrink it.

Rao and Matthew then explore AI's growing influence on security. Rao highlights why traditional rule based approaches cannot keep up with sophisticated threat actors who use AI to enhance phishing, social engineering, and lateral movement. He explains why companies must deploy AI powered detection tools, implement strict procedures, and train end users repeatedly to close the weakest link. His examples include major cyber incidents impacting insurers and how downtime directly affects revenue and operational stability.

Leadership is a key theme throughout the episode. Rao shares a story from his early career about how CEOs once viewed technology as simply the equipment department. This motivated him to change leadership perception and demonstrate IT's strategic value. His advice to CIOs and CISOs is clear: communicate wins, translate technical work into business outcomes, engage executives proactively, and shape organizational safety culture. Technology leaders must speak the language of the business and present themselves as contributors to revenue, efficiency, and protection.

The episode concludes with Rao's forward looking vision for the future of programming and AI. He describes his concept of NTH Generation Programming, a shift toward natural language interfaces that eliminate the need for traditional coding structures. For Rao, this is not an evolution but a revolution that will transform how systems are built, maintained, and optimized across industries.

CJ Covell is the Chief Information Officer at Everlast Roofing, a family owned American manufacturer specializing in metal building components used in residential, commercial, industrial, and agricultural construction. Since its founding in 1996, Everlast Roofing has expanded across multiple states, producing metal roofing and siding that power everything from pole barns to modern residential builds. CJ grew up inside the company, often learning technology alongside its evolution, and eventually developed a leadership style that blends hands on understanding with strategic direction. Today, he oversees technology, systems, process improvement, and digital transformation across a fast growing manufacturing footprint.

• How Everlast Roofing scaled from a small family business to a multi state manufacturer

• Why CJ believes technology should serve as a force multiplier for human ability

• How AI is transforming warehouse operations, logistics, and ERP workflows

• Why understanding the user experience is the foundation of great system design

• How Everlast used ChatGPT and Cursor to build a production ready warehouse system in weeks

• Why communication tools like Zoom and good audio equipment are essential for trust and connection

• How strong vendor relationships affect long term technology outcomes

• Why future leaders must continually experiment with AI to avoid falling behind

CJ Covell shares the origin story of Everlast Roofing and explains how a family business adopted technology from the earliest stages of the internet. Many longtime employees received their first email address through Everlast, which created a unique challenge as the company transitioned from simple office servers to modern systems requiring structured access control and disciplined IT strategy. CJ reflects on growing up inside the organization, helping solve computer issues as a child, and watching technology become a business critical function.

A major theme of this episode is the acceleration of AI and its ability to amplify human capability. CJ describes Everlast's challenge of managing a massive coil warehouse with thousands of steel coils and new employees lacking historical knowledge. Instead of hiring outside consultants or purchasing a costly logistics system, CJ and his team used ChatGPT to generate system specifications, ask context building questions, and outline a custom warehouse solution. Within three weeks, his team built a working application using Cursor that now allows any employee with a phone to find coils, scan barcodes, update information, and perform tasks with confidence. What would have taken six months to a year with traditional consulting was completed internally with greater accuracy and far lower cost.

CJ also discusses the importance of deep user empathy. He spent days performing warehouse tasks himself to understand friction points and workflow issues. By capturing every moment of friction and turning it into actionable design requirements, the team created a solution that improves decision making and eliminates guesswork. CJ emphasizes that most people do not make mistakes intentionally; they simply lack the right information at the right time. Technology becomes transformative when it removes barriers rather than creating new ones.

The conversation shifts toward communication and the role technology plays in building connection. CJ explains why tools like Zoom outperform other platforms and how simple investments in lighting, microphones, and camera placement create human centered virtual interactions. He even uses a teleprompter setup so his eyes align directly with the viewer, creating natural eye contact and improving trust. CJ points out that companies often resist small investments in communication technology despite spending thousands on travel for a single meeting. He argues that communication quality is the modern equivalent of showing up well dressed and prepared for an in person conversation.

CJ closes with a reflection on the future of AI and security. He notes that threat actors now use AI to mimic writing styles, create sophisticated phishing attacks, and exploit email weakness. As businesses rely heavily on email, AI driven threats force organizations to adopt AI powered defenses. Beyond security, CJ believes the rapid acceleration of AI means leaders must continually experiment, learn, and adapt. Falling behind even briefly could create a widening gap that becomes impossible to close.

Lemon Williams serves as the Chief Information Security Officer at Pine Gate Renewables, one of the nation's leading utility scale solar power developers and operators. With a background spanning Y2K era infrastructure, consulting, critical asset protection, and modern cybersecurity leadership, Lemon brings a rare blend of technical depth and operational awareness. He oversees both security and IT operations for a rapidly growing renewable energy organization that manages solar plants across 33 states. His experience navigating regulatory pressure, data concentration risks, operational resiliency, and AI enabled security tools gives him a comprehensive perspective on what security looks like in the evolving energy sector.

• Why renewable energy companies face unique risks tied to data concentration and flat organizational structures

• How combining IT operations and security leads to a resiliency focused model instead of a reactive cybersecurity model

• Why mid sized companies must treat every user as part of the security function

• How AI enabled tools can automate micro level adjustments and strengthen security posture

• Why data sharing with third parties expands breach exposure even if your own system remains uncompromised

• How to build better relationships with users through education instead of enforcement

• Why role based access control must evolve when employees wear multiple hats

• How the CISO role is shifting toward business partnership, internal consulting, and revenue protection

Lemon Williams explains why Pine Gate Renewables carries the same responsibilities as major utilities despite having a fraction of the staff. With a lean structure and flat teams, the company must carefully manage privilege, role combinations, and data concentration. Lemon outlines how a single compromised account in a mid sized organization can have wider consequences than in a highly compartmentalized enterprise, which creates the need for a more deliberate approach to access control.

A major theme of the conversation is the convergence of security and IT operations. Lemon shares how his teams merged into a single organization focused on resiliency rather than traditional cybersecurity boundaries. He explains that every role touching technology inevitably touches security, and that the organization functions better when analysts, sysadmins, and support staff think through the same lens. This shift allows Pine Gate Renewables to prevent issues earlier and support smooth operations even when incidents occur.

Lemon also dives deep into the challenges of data sharing across partners, vendors, legal teams, compliance groups, and internal departments. He describes how companies often underestimate how much sensitive information flows through routine work and why a third party breach can expose years of shared data. His team spends significant time understanding how information moves, what truly needs to be shared, and how to reduce unnecessary exposure through redaction, alternative delivery channels, and better automation.

Education and partnership drive much of Lemon's security philosophy. Instead of playing the role that staff fear, he and his team focus on being approachable problem solvers who embed themselves with operational groups. By explaining concepts like multifactor authentication, encryption, and role based controls in simple terms, they build trust and encourage employees to reach out early. This shift toward internal consulting has increased security's credibility and positioned the team as collaborators rather than blockers.

The second half of the episode explores AI enabled security tools that can detect unusual behavior, adjust access in real time, and monitor user patterns. Lemon sees significant promise in these systems, especially in environments with limited staffing. Tools that make thousands of micro adjustments per minute give teams more time for innovation, strategic planning, and measurable contributions such as reducing cyber insurance premiums. For Lemon, AI is not a threat but an accelerator that allows security teams to operate with greater precision and impact.

Mark Bentsen serves as the Chief Information Officer at CellGate Access Control Systems and is the Co Founder of Secure IVAI, an artificial intelligence managed service provider. His career includes decades of experience in logistics, banking software, healthcare technology, and security engineering. Mark spent ten years at FedEx in technology roles before transitioning into software development, AI integration, and cybersecurity work across multiple industries. His combined background in physical security, AI adoption, and enterprise software gives him a unique perspective on how organizations can secure remote properties, implement AI safely, and prepare for the next generation of intelligent systems. Today, Mark leads technology strategy at CellGate while supporting clients through Secure IVAI as they adopt AI in a practical, scalable, and secure way.

• How CellGate provides full stack access control using hardware, software, and cloud managed systems

• Why cellular to cellular failover is one of the hardest engineering challenges in security devices

• How Secure IVAI helps small and medium businesses adopt AI safely and securely

• Why many businesses feel overwhelmed when choosing where to begin with AI

• How Mark uses frontier models like Claude to talk directly to years of operational data

• Why verifying AI outputs is essential for trust and long term adoption

• How organizations can evaluate emerging AI products in a crowded market

• What the next phase of AI looks like as agentic systems accelerate

Mark Bentsen explains how CellGate solves one of the biggest problems in physical security: providing reliable access control in places where wired connections do not exist. CellGate devices operate in remote ranches, oil fields, and rural properties, relying entirely on cellular networks. Mark describes why switching between carriers is not as simple as choosing the strongest signal at any moment and why true cellular failover requires sophisticated engineering that most competitors have not mastered.

Mark also shares the origin of Secure IVAI, a managed service provider he co founded with a longtime friend who served as a chief information security officer. Their goal was to help businesses adopt AI responsibly, building real world solutions rather than theoretical prototypes. Mark explains how early reactions to AI ranged from skepticism to fear and why most companies struggled with one foundational question: where do we start. His work focuses on giving businesses a safe and structured entry point into AI adoption.

The conversation expands into how AI can be used today to query years of company data across tools like Fabric, Salesforce, and Jira. Mark describes how he asks natural language questions of millions of records and then verifies those results directly in the company's internal systems. He outlines how businesses can evaluate new AI products, why they should understand what a model was trained on, and how to test for reliability. He also explains why specialized models can outperform general purpose tools when they are trained on narrow, domain specific data.

Mark closes by discussing the future of agentic AI. True agents, he notes, are not simple workflow tools but systems capable of understanding goals, coordinating tasks, and making decisions with minimal oversight. With AI capabilities doubling roughly every seven months, Mark expects meaningful agentic systems to emerge within months, not years. He also emphasizes why professionals must develop horizontal awareness, stepping outside their own silo to drive business impact across the entire organization.

Glenn Rumfellow serves as the Chief Information Officer at Window World of Baton Rouge, part of the largest Window World operation in the United States. His career began with early exposure to programming on the TRS 80 and Apple II, followed by roles in mainframe programming, technical support, and extensive development work in Microsoft Access, SQL, and enterprise document imaging. Glenn joined Window World first as a consultant, then as CIO, and now leads the organization's technology strategy across four major markets. His work includes modernizing legacy systems, guiding cloud migrations, deploying AI driven tools, and supporting operational efficiency in a business that completes tens of thousands of home installations each year.

• How Glenn transitioned from early BASIC and Pascal programming into enterprise technology leadership

• Why Window World is modernizing a long standing Microsoft Access CRM and preparing for an Azure migration

• How data accuracy, reporting, and automation support a business completing tens of thousands of installations

• How AI powered tools like Samsara and Reila support driver safety, coaching, and sales performance

• How Glenn built a natural language query interface using an LLM to help executives access data

• Why operational scale requires strong APIs, data structures, and continuous reporting discipline

• How Window World uses analytics to measure installers, sales reps, regions, and marketing sources

Glenn Rumfellow shares how he went from tinkering with early computers to leading technology for the largest Window World operations in the country. His background across mainframe systems, enterprise imaging platforms, and complex Access and SQL applications shaped his approach to designing reliable systems that scale with the business.

He explains how a long standing Access based CRM supported the company for nearly two decades and outlines the ongoing transition into a modern web application backed by SQL and Azure services. Glenn describes the level of data movement, automation, and reporting required when a company handles tens of thousands of installations each year. API integrations, structured reporting, and database mail have become essential to keeping the operation efficient and accountable.

Glenn also highlights how AI is already embedded in their business. The team uses Samsara for real time driver safety alerts and video capture, and they recently adopted Reila to improve sales performance through coaching and analysis. In the IT department, AI tools assist with coding, documentation, and product research. Glenn even built a prototype LLM powered query tool so executives can access operational data through natural language. He also shares how the team evaluates AI call agents and considers long term opportunities for automation as the technology becomes more cost effective.