Matthew Connor
The Cyber Business Podcast
Welcome to The Cyber Business Podcast where we feature top founders and entrepreneurs and share their inspiring stories.
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Episodes
The Economics of Cybercrime and the AI Strategy Behind Getty with Isaac Straley - Ep 224 22.06.2026 35:51
Guest Introduction: Isaac Straley is the CISO of the J. Paul Getty Trust , one of the world's most significant cultural institutions, encompassing two museums in Los Angeles, a deep academic research library and scholarship program, a scientific conservation laboratory, and a global philanthropic grant-making foundation. Two months into his fourth CISO role, Isaac brings a career spent almost ent...
No Longer Exploratory: Building AI Governance for K12 with Desmond Grant - Ep 223 16.06.2026 39:44
Guest Introduction: Desmond Grant is the CIO of Littleton Public Schools , a high-performing school district located approximately 15 minutes southwest of the Denver metro area and recognized across Colorado and the nation for its academic outcomes. In his second year as CIO, Desmond oversees technology strategy, cybersecurity, and data governance for a district navigating the same funding pressu...
Building the School of the Future in Kansas with Rob Dickson - Ep 222 11.06.2026 29:48
Guest Introduction: Rob Dickson is the CIO of Wichita Public Schools , the largest school district in Kansas, serving just under 50,000 students across 87 schools and programs throughout the Wichita metro area. In a role that spans both operational and instructional technology, Rob oversees cybersecurity and infrastructure alongside a portfolio of forward-looking educational initiatives that incl...
From 45-Year Mainframe to AI Campus: Loyola's CIO on What Works with Alan Schomaker - Ep 221 08.06.2026 38:43
Guest Introduction Alan Schomaker is the CIO of Loyola University New Orleans, a Jesuit-based institution of approximately 5,000 students that includes a law school and sits on the Gulf Coast as one of four Loyola universities across the country. Five years into his tenure, Alan has led one of the more dramatic technology transformations in higher education, taking the university off a 45-year-old...
You Can't Outrun a Script: AI Security in a Law Firm with Michael Massey - Ep 220 03.06.2026 27:12
Guest Introduction Michael Massey is the CISO at Reminger Co LPA , a defense-focused law firm handling medical malpractice defense, workers compensation defense, and insurance defense across a large portfolio of client matters. With a background that includes time at IBM Watson Health during what he describes as the early days of AI in healthcare analytics, Michael brings a practitioner's perspect...
Why AI Rollouts Fail and What Employers Did Differently with Kelley Kage - Ep 219 01.06.2026 41:16
Guest Introduction Kelley Kage is the CIO of Employers Insurance, a 113-year-old workers compensation carrier operating nationwide that recently expanded into excess workers compensation. Overseeing technology, data, product management, and cybersecurity, Kelley has led one of the most deliberate and results-driven enterprise AI rollouts featured on this podcast, achieving 77% adoption and 90% tra...
Machine Speed Attacks, Voice Agents, and Why Bad AI Excuses Fail with Keith Trawick - Ep 218 27.05.2026 37:41
Guest Introduction Keith Trawick is the CIO of Stretch Zone , a practitioner-assisted stretching franchise with more than 420 locations across the country and another 75 to 80 expected to open this year. He joined the organization as employee number one when it made the move from boutique wellness service to scalable franchise brand roughly 12 years ago, helping build the technology infrastructu...
Why the Credit Union Peer Network Is a Security Advantage Banks Cannot Buy with Nico Stein - Ep 217 25.05.2026 42:30
Guest Introduction: Nico Stein is the SVP of IT and Operations at Signal Financial Federal Credit Union , a community-based, member-owned credit union headquartered in Maryland with branches across the DC and Virginia region. With more than 12 years at Signal Financial, he oversees everything from laptops to cybersecurity to the financial core, and has built a reputation in the credit union commun...
Deepfakes, Demos, and the Real Cost of a False Sense of Security with Chris Pacifico - Ep 216 20.05.2026 54:15
Guest Introduction Chris Pacifico is the Director of IT at Rehab Medical , a durable medical equipment provider that gives people with mobility challenges access to everything from basic wheelchairs to advanced power chairs operated by eye movement. With a background spanning healthcare IT, technical writing, and hands-on security work, Chris brings a practitioner's perspective to AI adoption, bud...
AI Is Draining the Grid: Behind-the-Meter Power Solutions with Tony Uttley - Ep 215 18.05.2026 51:09
Guest Introduction: Tony Uttley is the CEO of Enginuity Power Systems , a behind-the-meter cogeneration company delivering combined heat and power solutions to hospitals, schools, farms, and multi-family housing facing the full force of America's coming energy crisis. An engineer by training, Tony spent a decade at NASA's Johnson Space Center, seven years at the Boston Consulting Group, and near...
Why Silence After a Breach Helps the Hackers with Scott Dickinson - Ep 214 14.05.2026 37:37
Guest Introduction: Scott Dickinson is the first-ever CISO at AnMed Health, a not-for-profit hospital system in Anderson, SC with three main hospitals and a growing network of emergency care facilities. He brings a career spanning military intelligence, the FBI, the Department of Commerce, the Department of Defense, and multiple state agencies to one of the most high-stakes environments in cyberse...
Breaking Things on Purpose: An Honest Take on AI Readiness and Leadership with Shawn Hamm - Ep 213 11.05.2026 55:30
Guest Introduction Shawn Hamm is a cybersecurity leader with three decades of IT experience who is currently making the deliberate move from Director of Cybersecurity into the CIO seat. With a background spanning hands-on technical work, consulting, security leadership, and hiring, he brings a practitioner's perspective to both the technology and the human side of organizational leadership. His wo...
Why Machine Learning Is the Unsung Hero of the AI Era with Ben Wilcox - Ep 212 06.05.2026 30:47
Guest Introduction: Ben Wilcox is the CTO and CISO at ProArch , a Microsoft partner organization with 20 years of experience helping companies across healthcare, manufacturing, energy, and independent software development take data to intelligence. In his dual role, Ben leads both the technology and security functions, working directly with clients to build AI-ready foundations, deploy agentic w...
Defending Critical Infrastructure in the Age of AI Attacks with Sean Murphy - Ep 211 04.05.2026 40:12
Guest Introduction: Sean Murphy is the Senior Vice President and Chief Information Security Officer at BECU, the 4th largest credit union in the United States and the largest community-based credit union in the country, with approximately $30 billion in assets. With more than 7 years at BECU, Sean leads a security organization of 60 professionals spanning risk management, identity and access manag...
Why Insecure AI Is Just as Dangerous as No AI with Shannon Brewster - Ep 210 29.04.2026 41:45
Guest Introduction Shannon Brewster is the CISO at YipitData, a market research firm providing real time analytics and competitive intelligence, including Spendhound, a product that helps IT professionals track SaaS spend, benchmark pricing, and manage contract renewal cycles. Shannon joined in December 2025 and also leads the enterprise IT organization. She is a board member of ISC2 and came to t...
Three Weeks to 45 Minutes: What Real AI Adoption Looks Like in Insurance with Barninder Khurana - Ep 209 27.04.2026 30:36
Guest Introduction Barninder Khurana is the Chief Information Officer at Patriot Growth Insurance Services, a full service national insurance agency operating across 29 states with approximately 2,100 employees and 160 locations, ranked as a top 25 insurance agency in the United States. Three months into his CIO role at the time of recording, Barninder brings a career that started in 1997 with a s...
Why Your SaaS Vendor's New AI Button May Be Your Biggest Security Risk Right Now with Fletus Poston III - Ep 208 22.04.2026 34:45
Guest Introduction Fletus Poston III is the Director of Security and Systems Architecture at 3D Systems Corporation, one of the world's leading additive manufacturers. In his role, he oversees the overall architecture for both the cybersecurity and IT functions, including infrastructure, cloud, and the governance models that tie them together. 3D Systems builds commercial 3D printers from the boar...
Why Fighting AI in the Classroom Is the Wrong Battle with Chris Campbell - Ep 207 20.04.2026 37:02
Guest Introduction Chris Campbell is the CIO at DeVry University, a career-aligned institution focused on delivering education in high-demand technology fields that translates directly into workforce-ready skills. In his role, Chris leads technology, cybersecurity, and digital innovation across the university, with a current focus on integrating AI into both operations and curriculum in ways that...
Maritime Cybersecurity, AI Governance, and the Threats No One Sees Coming with Amit Basu - Ep 206 15.04.2026 36:35
Guest Introduction Amit Basu serves as both CIO and CISO at International Seaways, one of the world's largest publicly traded tanker companies, listed on the New York Stock Exchange under ticker INSW and headquartered in New York City. The company owns and operates 75 large ocean going tankers that transport crude oil and petroleum products across major global routes. In his dual role, Amit is res...
The Arms Race, the Energy Gap, and the Ethics of Teaching AI to Be Good with Alex Dalay - Ep 205 14.04.2026 33:00
Guest Introduction Alex Dalay is the CISO at IDB Bank, a New York-headquartered commercial, private banking, and broker dealer institution with more than 70 years of history. As the security leader of a financial institution that sits squarely in the crosshairs of modern threat actors, Alex brings a perspective grounded in operational reality rather than theoretical frameworks. His approach to sec...
Role-Based AI, Culture-First Hiring, and the Future of Human-Centered Tech with Laurel Cipriani - Ep 204 08.04.2026 59:05
Guest Introduction Laurel Cipriani returns to the Cyber Business Podcast for a second conversation that goes deeper and broader than the first. As CIO at AffirmedRX , a transparent pharmacy benefits management company and public benefit corporation legally obligated to put patients ahead of profits, Laurel brings a background unlike almost any other CIO in the industry. She trained in psychology,...
Why Every CISO Must Use AI Now and How to Do It Without Losing Control with Greg McCord - Ep 203 06.04.2026 37:33
Guest Introduction Greg McCord is a career security leader operating across two roles simultaneously. As CISO at Lightcast.io, a leading labor market analytics firm, he protects one of the most data-intensive organizations in the workforce intelligence space. As founder and CISO of McCord Keystone Advisory, launched in late 2025, he extends fractional CISO services to small and mid-sized businesse...
Identity Is the New Perimeter: A Cybersecurity Director's Playbook with Jason Lawrence - Ep 202 01.04.2026 37:49
Guest Introduction Jason Lawrence is the Cybersecurity Director at Yancey Brothers, the oldest Caterpillar dealer in the United States and a company that has been in business since 1914. As the first person to hold this role at the organization, Jason is building the cybersecurity program from the ground up, reporting directly to the CIO. Before joining Yancey Brothers, Jason built a career spanni...
How AffirmedRX Is Using Technology to Fix a Broken Healthcare System with Laurel Cipriani - Ep 201 30.03.2026 48:03
Guest Introduction Laurel Cipriani is the Chief Information Officer at AffirmedRX , a transparent pharmacy benefits management company built on a mission to make medications accessible and affordable for everyone. A clinician by training and a registered nurse originally, Laurel brings a rare combination of frontline healthcare experience, executive technology leadership, and global policy engagem...
The Two AI Attack Paths Every Security Leader Needs to Understand Now with Sinan Al Taie - Ep 200 25.03.2026 53:28
Guest Introduction Sinan Al Taie is the Cybersecurity Manager at Master Electronics, a leading global authorized distributor of electronic components with more than half a century of history as a family owned business headquartered in Phoenix, Arizona. His path into cybersecurity is one built from firsthand experience, having transitioned into the field after being hacked himself while working as...
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