Podcast Summary: Risky Bulletin – Trail of Bits Going All-In on AI

Date: February 8, 2026
Host: Tommy Wren
Guest: Dan Guido (CEO, Trail of Bits)

Episode Overview

In this sponsored interview, Tommy Wren talks with Dan Guido, CEO of Trail of Bits, about the company's aggressive shift toward AI-first operations in cybersecurity consulting. Dan explains the rationale behind this decision, details practical implementations within the company, and discusses the profound effects AI is having—and will continue to have—across the security industry. The conversation is candid, practical, and forward-looking, focusing on the systematic internal changes Trail of Bits is adopting to ensure continued leadership as the industry rapidly evolves.

Key Discussion Points & Insights

1. AI in Security: Not Just a Buzzword

• [00:14–01:44]
  • Trail of Bits isn’t just experimenting with AI; it’s fundamentally reorganizing itself to be “AI native.”
  • Rather than giving open-ended problems to LLMs, Trail of Bits is building tightly-scoped “skills” guiding AI with their own workflows, tools, and verification steps.
  • These skills leverage the broad knowledge base of LLMs, but crucially tailor that ability to the specific context, environment, and goals of the security workflow.
  • Dan Guido:

    “These are specific bite sized pieces of behavioral guidance that you give to Claude because the LLM is already trained on the entire universe of knowledge [...] what you’re doing is you’re reminding it: here’s how to use that information, here’s how to operationalize it, here’s the tools that you can call, here’s what you should do with the output…”
    ([01:05])

2. Why This Shift is Existential

• [01:46–04:04]
  • Dan frames the move as existential—not simply a competitive advantage, but necessary to justify the company’s existence in the near future.
  • He predicts that consulting, in particular, will be dramatically affected, with obvious discrepancies between firms that utilize AI effectively and those that do not.
  • Publication of tools and internal techniques is part of Trail of Bits’ philosophy—both for their own benefit (discoverability by agents, not just humans) and to drive industry-wide standards.
  • Dan Guido:

    “This is existential for me. I am fully bought in that the entire industry is going to change over the next year... I want to make sure we’re at the front riding that wave so that we can justify our continued existence.”
    ([03:16])

3. Internal AI Adoption: Process, Not Projects

• [04:13–07:05]
  • Adopting AI isn’t about layering tools on current workflows—it’s about organizational transformation.
  • Triggered by significant improvements in AI (i.e., Claude Code, Opus 4.5), Dan describes a “click” that made him trust and depend on new AI systems.
  • Trail of Bits is actively rethinking content delivery: ensuring documentation and competitive differentiators are agent-discoverable rather than just human-readable.
  • New marketing approach focuses on providing content in structured, machine-consumable forms (markdown, comparison tables, etc.) to ensure AI agents can access and recommend their offerings.

4. AI as the Next Industrial Revolution for Companies

• [07:05–09:14]
  • Dan predicts “every company” that wants to thrive will need to adopt similar approaches, not just a vanguard minority.
  • Companies with tailored, internal AI-driven systems will out-ship and out-perform competitors.
  • AI is democratizing advanced security tasks, making previously daunting practices (like formal verification and comprehensive testing) feasible at scale and speed.
  • Dan Guido:

    “For people that can build the systems to fully adopt AI, they will be able to be more responsive to customer needs… Internally, for our team, AI has put things like formal verification in reach for a much larger number of projects…”
    ([07:20])

5. Concrete Examples: Automating Away the Grind

• [09:14–11:13]
  • Trail of Bits is automating time-consuming review tasks, such as bug fix verification, using orchestrated AI agents guided by internal coding standards and best practices.
  • What used to take days of expert work (e.g., verifying all fixes in a codebase) can be done reliably and rapidly, with human expert oversight taking only a fraction of the original time.
  • Dan Guido:

    “It’s possible for us to take what used to be a three-day process and turn it into an automated action that an expert can oversee in about 10 minutes.”
    ([10:33])

6. Rigor, Verification, and Trust

• [11:56–14:34]
  • The cornerstone for safe deployment of AI-driven automation is robust verification.
  • Dan ensures every Trail of Bits project includes stringent pre-commit hooks, 100% test coverage, aggressive linters/formatters, and type checks.
  • For more complex outcomes (exploits, not just code correctness), proprietary “verifiers” are needed to check task success (e.g., confirming an exploit actually works). Initially, much of this evaluation is still human-assisted, but the aim is to automate more over time.
  • Dan Guido:

    “What AI really needs is feedback that the job was done the right way… you have 100% test coverage, and you have all the most pedantic linters turned on with no warnings whatsoever. Everything’s an error.”
    ([13:06])

7. Shifting Everything Left: Feedback and Automation

• [15:06–18:17]
  • Fast, continuous, and automated feedback loops are prioritized: optimizing CI, pushing checks to pre-commit, and ensuring conformance via AI across hundreds of repositories.
  • Adoption of strict language standards (favoring type-safe languages like TypeScript) and policy enforcement is key.
  • AI isn’t just performing security tasks—it’s enforcing and disseminating new company standards and best practices across the organization, compounding productivity and learning.
  • Notable moment: Regular peer-led “learning sessions” enable rapid dissemination of new tools/features (e.g., within hours of Claude CoWork release).

Notable Quotes & Memorable Moments

• “This is existential for me… the entire industry is going to change over the next year.” —Dan Guido ([03:16])
• “It’s possible for us to take what used to be a three-day process and turn it into an automated action that an expert can oversee in about 10 minutes.” —Dan Guido ([10:33])
• “The winners in 2026 are going to be the people that figure out how to compound their effort through the process they have internally…” —Dan Guido ([17:07])

Timestamps for Key Segments

• 00:14 — Dan outlines what “going all-in on AI” means at Trail of Bits.
• 01:46 — Explanation of specific and practical AI “skills” used in security workflows.
• 04:04 — The shift to AI-native as existential and strategic for consulting.
• 07:05 — Why every company, not just consultancies, will need to adapt in similar ways.
• 09:51 — Transforming days-long review tasks into automated, validated workflows.
• 11:56 — The necessity of rigorous, automated verification and quality gates.
• 15:06 — Importance of rapid, automated feedback and internal process automation.

Overall Tone & Takeaways

Candid, pragmatic, and at times urgent, Dan Guido’s insights convey a sense of both inevitability and optimism about AI-driven transformation in cybersecurity. While he notes the excitement and terror that come with such rapid change, the message is clear: companies that adapt and reinvent their internal processes for continuous, rigorous, AI-driven operation will dominate, while those who delay risk irrelevance.

Final words from the host:
“I don’t know whether to be terrified, excited or inspired, but I’m looking forward to seeing what happens.” ([18:17])

End of Summary