Risky Bulletin Sponsored: Trail of Bits going all-in on AI
Feb 8, 2026
Dan Guido, CEO of Trail of Bits and cybersecurity leader applying AI to security engineering. He explains reorganizing the firm to be AI-native and publishing Claude skills. He describes teaching LLMs operational guidance, automating reviews and verifiers, and scaling AI-driven workflows to speed testing, audits, and CI.
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Skills Guide Agents To Use Knowledge
- Trail of Bits packages guidance as small behavioral 'skills' that steer large language models to use existing knowledge correctly.
- Skills teach the agent tools, workflows, and how to operationalize its pre-trained knowledge for security tasks.
Rework Processes To Be AI-Native
- Make your company AI-native by building workflows, verification, and privacy-safe processes before widespread adoption.
- Publish and standardize successful patterns so agents and people can reuse them across the organization.
AI Will Separate Fast From Slow Consultancies
- AI adoption will sharply differentiate consultants in 2026 by speed and quality of output.
- Firms that prove rigor and trustworthiness in AI-driven work will win more engagements.