Kirby Winters

Guest

Information Security Practice Leader at TechCXO

Joining us in the Sky Lounge today is Kirby Winters—tech entrepreneur, cybersecurity expert, and partner at TechCXO. Kirby takes us through his journey from telecom to launching (and selling) his own business before diving back into consulting. Kirby breaks down the world of cybersecurity, from social engineering scams to compliance audits, and how AI is changing the game. Along the way, he shares stories of leadership—both good and bad—that have shaped his approach to balancing innovation and risk. Kirby J. Winters is a leader in the cybersecurity and technology-based communications industry with extensive experience across multiple sectors. Since 2016, he has led the Information Security Practice at TechCXO, working with healthcare, banking, and Department of Defense clients. His leadership has delivered innovative solutions, including advanced Electronic Medical Record systems, AI-driven practice management, and wireless health monitoring tools. Kirby has held executive positions across numerous industries, with a focus on Technology Product Management, Information Security Certifications, Web and Mobile Product Development, and interim CISO/CTO/CIO roles. He served as interim CISO for a $20b bank, implementing significant improvements in security governance and compliance, and still serves on the bank’s Cyber Security Advisory Board.

Episodes with Kirby Winters

July 22, 2026

Parallel Entrepreneurism: Shipping Startups Side by Side | Kirby Winters, Ep 50

Kirby Winters discusses launching multiple ventures simultaneously using AI-powered development, including Cyber Savi (a compliance automation platform), a vodka brand, and Unshucked (an oyster tracking app). He explains how agentic AI enables building production-ready software in weeks instead of years, the shift from consulting to outcome-based services, and strategies for selling cybersecurity compliance tools through MSP channel partners.

Agentic Framework Architecture AI Adoption Paradigm Shift AI Workflow Automation+5 more

October 2, 2024

Scout Skills, Leadership Hacks, and Smart Security in the Age of AI | Kirby Winters, Ep 17

Kirby Winters, fractional CISO at TechCXO, discusses his journey from telecom to cybersecurity consulting, emphasizing leadership lessons from Eagle Scouts and entrepreneurship. He covers the evolving threat landscape—from social engineering to AI-enhanced phishing—and explains how fractional security leadership helps SMBs navigate SOC 2, HIPAA, and CMMC compliance without full-time hires. The conversation explores VPN evolution, cyber insurance realities, and the critical need for proactive security planning before customer mandates or breaches force action.

AI-Enhanced Cyber Threats Business Consulting CMMC Certification+5 more

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