Claude Code Looked Right but Missed $800K - Natalia Connolly & Kevin Madura, AlixPartners

Natalia Connolly and Kevin Madura of AlixPartners pointed Claude Code at a real post-merger procurement analysis: hundreds of vendors and more than 40,000 contracts. The first answers looked complete, but one total was off by about $800,000 and a key renewal deadline was a month late. They walk through why: long contracts that silently failed to process, amendments that weren't linked to their parent contracts, and rate tables split across pages. They explain how a five-stage pipeline that structures the data first, plus custom tools with built-in business rules, made every answer traceable to its source. They also share lessons on clear access errors, de-duplicating savings found by parallel agents, and giving the agent context about what the business is already doing. Chapters: 0:00 Intro 0:52 The deal: two companies, 40,000 contracts 2:30 Answers that looked right 3:29 Why contract data is messy 5:46 A five-stage processing pipeline 7:08 Charts, tables and structured output 8:26 Custom tools with built-in business rules 10:20 Packaging what works 11:14 Lesson: the wrong date 11:59 Lesson: orphaned amendments 13:25 Lesson: access errors look like zeros 14:37 Lesson: de-duplicating savings 16:04 Lesson: know what the business is already doing 17:37 Takeaways Natalia Connolly Kevin Madura https://www.alixpartners.com Join us in SF for the second annual AIE CODE summit: https://aie.codes our last flagship summit of 2026. Applications live now!