Ryan Cummings

Ryan has built and led security programs from the ground up across healthcare, insurance, senior living, and defense — standing up global information security programs across international teams, leading HITRUST/HIPAA/SOC 2 Type 2 compliance through post-acquisition transformations, and delivering first-ever SOC 2 reports with zero findings or management exceptions. Earlier in his career he led IT security and infrastructure in high-stakes, regulated government and healthcare environments.

As a current CISO & Head of AI/Automation, Ryan runs both disciplines at once: building inaugural SOC 2 Type 2 programs and AI governance frameworks, and separately architecting AI-driven operating systems for new business lines — using autonomous AI agents while embedding privacy controls and secure-AI-design principles directly into the architecture. That combination, security leadership and hands-on AI system-building under one person, is what he brings to every virtual CISO engagement.

That AI experience isn't theoretical. Ryan has delivered firm-wide AI enablement training for organizations outside his own, connected AI agents into the CRM, email, and document systems a business already runs on, and carried AI proof-of-concepts through security review and reliability testing into shipped, production-grade services — the practical, ship-it track record behind DGC's AI Enablement, AI Integrations, and Enterprise AI Readiness services.

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