02 · Diligence

Technology & AI Diligence

Pre-investment and post-close technical review for investors deciding whether a thesis holds, and operators figuring out what they actually bought.

What this is

Diligence engagements compress two to four weeks of intensive review into a deliverable that an investment committee, an operating partner, or a board can act on. We examine the architecture, the team, the roadmap, the data, the AI systems, and the regulatory exposure. We tell you which risks are priced into the deal, which aren’t, and which are reasons to walk.

We work directly with the IC or the operating partner. The company is informed, briefed, and given a fair chance to respond. The deliverable is a written report that travels.

What we examine

  • Architecture and platformSystem diagrams, technology choices, dependency graph, observed performance under load, technical debt, and the cost to run.
  • Engineering team and leadershipOrg chart, key-person risk, hiring posture, recent turnover, and an honest assessment of the senior engineering bench.
  • Roadmap viabilityCost to deliver what has been promised against what the team can plausibly do in the timeframe stated.
  • Data assetsData quality, provenance, access controls, and the gap between what is claimed and what is usable.
  • AI and ML capabilitiesModel risk, data dependencies, vendor lock-in, and the regulatory exposure of automated decision-making.
  • Regulatory and complianceSector frameworks like HIPAA, PCI, and SOC 2. Jurisdiction-specific obligations including NYC Local Law 144, EU AI Act, and GDPR. Litigation risk in AI-driven hiring or pricing.

When this fits

  • Pre-investment diligence for PE, VC, and angel investors.
  • Post-close technical review for new portfolio companies.
  • Periodic check-ins on existing portfolio companies between board meetings.
  • Pre-sale preparation when an operator is preparing to be diligenced themselves.

How it’s structured

  • Two to four week sprint with fixed scope and fixed fee.
  • Reading the artifacts first, then interviewing the team.
  • Written diligence report with priced findings, organized by severity.
  • Closing call with the investment committee, the operating partner, and the company CEO and CTO.
  • NDA available on request before any portfolio detail is shared.

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