Built on identity, cloud, and AI security experience
cybersecurity303 is a Colorado-based security practice. We work with teams whose infrastructure lives in the cloud, whose access is federated across a dozen tools, and whose newest identities aren't people at all — they're services, agents, and API keys.
Riley Webb, CISSP
Riley Webb, CISSP, is the Lead Consultant at Cybersecurity303, bringing more than 25 years of experience across enterprise IT, cybersecurity, identity, cloud architecture, consulting, professional services, and managed services.
Riley's background spans hands-on engineering, enterprise architecture, consulting, professional services, presales, delivery, and managed services leadership. He has helped organizations design and modernize workforce identity, customer identity, IAM, IGA, PAM, passwordless authentication, cloud security, and identity managed services across complex enterprise environments.
His experience includes technical and leadership roles with organizations including Okta, Deloitte, and Optiv, along with extensive work across AWS, Microsoft Entra ID, Ping Identity, SailPoint, Saviynt, CyberArk, BeyondTrust, Delinea, Auth0, Duo, Yubico, and other identity and security platforms.
Riley holds CISSP, AWS Solutions Architect, Okta Administrator, and CSA Trusted AI Safety Expert credentials. His current focus includes the intersection of identity, cloud infrastructure, non human identity, AI security, and agentic AI.
Riley established Cybersecurity303 to provide practical identity, cloud, and AI security expertise without the overhead and complexity of a large consulting firm.
Why we exist
Security programs built around a human logging in with a password don't map well to how modern systems work. A single application today might involve a person, an SSO session, a workload identity, a CI/CD pipeline, and an AI agent calling an internal API — each with its own credentials, its own blast radius, and its own way of quietly accumulating more access than it needs.
We started cybersecurity303 to work on that problem directly: helping teams secure cloud infrastructure, get identity and access right, and adopt AI without losing track of what it can touch.
Security architecture should enable the business
Cybersecurity303 focuses on practical security architecture that organizations can actually operate. The goal is not to add controls for the sake of adding controls. It is to reduce risk while making identity, cloud, and AI environments easier to govern, support, and scale.
Principles we hold to
Least privilege, actually enforced
Access should match need, not convenience. We design policy that's specific enough to matter and simple enough to maintain.
Every identity is in scope
Service accounts, API keys, and AI agents get the same scrutiny as human users — because attackers already treat them that way.
Something concrete, every time
No shelfware. Every engagement ends with something usable: a fixed policy, a documented architecture, a runbook.
Plain explanations
You should understand exactly what changed and why — no security theater, no jargon for its own sake.
Want the details on a specific engagement?
Explore our six service areas.