Ruminations from the Cyber Hat

Get leading edge advice and current insights into the complex world of cybersecurity, agentic AI and robotic automation technologies for startups to Fortune 1000 companies.

ABOUT ME

I'M A CYBERSECURITY LEADER AND AI BUILDER WHO LOVES HATS

Welcome to the digital corner of Kirby Winters—where cybersecurity meets coffee-fueled problem-solving and two decades of tech battle scars become your competitive advantage. From co-founding startups in basement offices to steering a $20 billion bank's security program through regulatory rapids, I've spent my career translating the chaotic world of compliance frameworks (yes, even HIPAA and CMMC) into strategies that actually work for real humans running real businesses. Whether I'm helping healthcare organizations navigate HITRUST mazes, advising boards on security postures, or explaining why your intern's bad password habit is giving your CISO nightmares, my mission is simple: make technology and security feel less like an intimidating mountain to climb and more like the strategic superpower it should be. So grab your beverage of choice, settle in, and let's demystify this ever-evolving world of tech, security, and compliance together—one thoughtful, occasionally irreverent blog post at a time.

7000+

PROJECTS

1200+

HAPPY CLIENTS

10K+

CUP OF COFFEE

100+

AWARDS WON

MY SERVICES

COMPLIANCE AS A SERVICE, AGENTIC AI DEVELOPMENT, CYBERSECURITY STRATEGY.

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CYBERSECURITY LEADERSHIP

Through a team-based approach leveraging proven tools and playbooks, our team helps customers transform security from a compliance checkbox into a strategic advantage, implementing governance frameworks that reduce IT security budgets, lower insurance premiums, and mitigate litigation risks while maintaining robust protection.

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AGENTIC AI CREATION

Our proven expertise in Agentic AI development and delivery, agile methodologies, requirements gathering, and systems integration provides the foundational framework needed to design, build, and deploy autonomous AI systems that solve real business problems—not just impressive demos.

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SECURE PRODUCT DESIGN

The team's approach to secure product design is rooted in a rare combination of hands-on development leadership and deep information security expertise, ensuring that privacy and protection are embedded from conception rather than bolted on as afterthoughts.

Who we are

Our Team

Kirby's team-based approach to cybersecurity transforms the traditionally isolating world of compliance and security management into a collaborative partnership that empowers client organizations rather than overwhelming them. Recognizing that effective security requires buy-in across every level of an organization—from the C-suite to IT teams to end users—his team deploys proven tools, playbooks, and methodologies that provide structure while remaining flexible enough to adapt to each client's unique culture, resources, and risk profile.