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Dan Guido

Summary

Dan Guido is the CEO and founder of Trail of Bits, a cybersecurity consulting firm. In March 2026, he delivered a talk at [un]prompted (the AI security practitioner conference) and published a blog post detailing how Trail of Bits transformed into an AI-native organization in roughly one year, achieving measurable results including 94 plugins, 201 skills, 84 specialized agents, and auditors finding 200 bugs/week. He has open sourced most of their tooling under the trailofbits GitHub organization.

Key Facts

  • Role: CEO and founder of Trail of Bits
  • Open source org: trailofbits (GitHub)
  • Publications: "How we made Trail of Bits AI-native (so far)" (blog.trailofbits.com, Mar 31, 2026); adapted from talk at [un]prompted 2026
  • Key open source tools: trailofbits/skills, trailofbits/claude-code-config, trailofbits/dropkit, trailofbits/slither-mcp

AI-Native Leadership

Guido's approach to AI adoption is notable for addressing psychological barriers directly:

  • Built a maturity matrix to counter self-enhancing bias
  • Framed AI as identity upgrade rather than identity threat (experts become "more permanent")
  • Wrote an AI Handbook that explains the risk model behind decisions, addressing opacity
  • Recognizes the existential question AI poses to the consulting business model ("the question shifts from how many hours did the auditor spend to did the auditor know where to point the agents and which findings are real")

Sources