Ryan Cummings

Leading both AI and security, Ryan ran both disciplines at once: architecting AI-driven operating systems for new business lines (using autonomous AI agents with privacy controls and secure-AI-design principles embedded directly into the architecture) and building the company's AI governance framework and inaugural SOC 2 Type 2 program so the business could stand behind them. That combination is why his AI work ships: it's built by someone who has also been the person who has to approve it.

His 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 Automation, AI Integrations, and Enterprise AI Readiness services.

Why the AI work clears review: a long security track record underneath it. 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, building two SOC 2 Type 2 programs from zero that have never had a finding, and taking an inherited program with prior findings through its first clean report. Earlier in his career he led IT security and infrastructure in high-stakes, regulated government and healthcare environments.

DreiBerge is German for “three mountains”: Ryan has three kids, each named after a mountain.