Playbook

AI in Underwriting: Early Proof Points in 2025

How AI tools are being applied to covenant tracking, monitoring, and deal screening.

Published Sep 6, 2025 • 5 min read

TL;DR

1) Where AI is working now (and why)

Best-fit workflows are repetitive, document-rich, and have crisp acceptance criteria. That’s covenants, portfolio monitoring, and high-volume screening.

Operator note: Success = constrained outputs + deterministic guardrails + page-level cites.

2) Proof points teams actually believe

3) Common failure modes

4) Implementation playbook (90-day cut)

  1. Weeks 0–3: Pick one workflow; define JSON schema; build validator + cites on 50–100 gold examples.
  2. Weeks 4–8: Reviewer UI with side-by-side PDF, confidence, one-click edits; push to trackers/BI.
  3. Weeks 9–12: Monitoring jobs + alert routing; start time-saved and miss-rate scorecards.

5) Data, governance, and security

6) What to watch into H2 2025

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