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

Ep 50 - Kirby Winters —Parallel Entrepreneurism: Shipping Startups Side by Side

Kirby Winters discusses his transition from management consulting to building Cyber Savi, a compliance and cybersecurity firm leveraging AI agents to automate audit preparation and security operations. He explains how agentic AI enables rapid development of multiple software products simultaneously, including compliance tools, dark web monitoring, and consumer apps like Unshucked (an oyster rating platform) and a vodka brand—all built using the Velocity Process development framework.

Agentic Framework Architecture AI Coding Acceleration AI Workflow Automation+7 more

October 2, 2024

Ep17 - Kirby Winters — Scout Skills, Leadership Hacks, and Smart Security in the Age of AI

Kirby Winters, fractional CISO at TechCXO, discusses his journey from telecom to cybersecurity consulting, emphasizing leadership lessons from Boy Scouts and entrepreneurship. He covers the evolving threat landscape, social engineering attacks, cyber insurance challenges, and compliance requirements like SOC 2 and CMMC. The conversation explores how AI is amplifying security risks and the growing need for fractional security leadership in small to mid-sized businesses.

AI-Enhanced Cyber Threats CMMC Certification Fractional Leadership+4 more

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