Caleb Crable

Caleb Crable is a Principal AI Red Team Engineer at a publicly traded life insurance company, where he attacks production AI deployments and the identity infrastructure underneath them. Before this he spent four years on the red team at BILL, running authorized engagements against critical financial infrastructure and the company's AI support platform, with a focus on prompt injection, tool abuse, and credential exposure in LLM pipelines.

Earlier in his career Caleb spent three years with Cylance Professional Services delivering full-scope red team engagements for clients in every business sector. Before consulting he was a senior malware analyst at Cylance and The Media Trust, doing deep file analysis, reverse engineering, and incident reconstruction, and serving as a research associate on the whitepaper "Influence Sketching: Finding Influential Samples in Large-Scale Regressions." With over 14 years in offensive security, he brings a practitioner's instinct to every layer of the stack, from physical entry and social engineering to AI red teaming and ML research.