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The eval setup nobody on my team wanted to build

Two-person shop, building a doc-extraction pipeline for invoices. For six weeks we shipped on vibes: I'd tweak a prompt, my cofounder would eyeball ten PDFs, we'd ship. Customer churned in March after we silently regressed on a vendor whose invoices use a two-column layout. The prompt change that helped scanned receipts broke that one customer, and we had no way to know. I spent a weekend wiring up a dumb eval harness. 140 labeled invoices, exact-match on line items, fuzzy on totals, runs in CI on every prompt change. Took maybe 14 hours end to end. Caught three regressions in the first month. The part I want to flag: I resisted this for weeks because it felt like premature infrastructure for a startup. It wasn't. The moment you have more than one customer with different document shapes, your head stops being a sufficient eval. I think founders skip evals because they confuse "move fast" with "don't measure." The teams I see shipping agentic stuff well treat eval sets as the actual product asset. The prompts are disposable.
28·linh_nguyen·

3 comments

0laylahaddad·2mo
Same story on our side. Got pushback for weeks until I ran a 50-doc benchmark by hand and showed the senior associates that the model was missing indemnity clauses in roughly 1 in 7 contracts. Suddenly everyone had time to help label.
0ZolaNdlovu·2mo
Built one for a two-person editorial shop last fall because clients kept rejecting drafts for reasons we couldn't pin down. The annoying part wasn't writing the rubric, it was getting myself to actually run it on outputs I already felt good about. Curious whether the author's team checks evals before sending to the client or only when something blows up.
0AishaKapoor·1mo
We finally bit the bullet after a model swap silently regressed our intake summarizer and three account managers caught it before QA did. Took two sprints to wire up a golden set of 80 labeled tickets and a nightly diff report, and now nobody on the team wants to ship without it. The hard part wasn't the tooling, it was getting legal to sign off on storing the labeled prod samples.