If you have conversation data — sales calls, support tickets, customer check-ins, emails, internal slack conversations — you’ve likely tried to “just point Claude at them” to get insights in the last six months. Feels like a fairly obvious thing to do in 2026.
The problem is that “pointing Claude at them” could mean many different things — each with their own tradeoffs and set of decisions.
You can point to the chat app at your warehouse.
You can point an agent at it.
You can write your own code against the API — naively, or with a map-reduce pipeline, or through the Batch API, or with RAG.
You can point Claude at pre-enriched data.
You can buy a product like Rippit.
These setups all use similarly performant LLMs and they all produce confident, good-looking answers.
For each setup though there is a set of tradeoffs:
- How long does it take to get an answer?
- How accurate do I need the answer to be?
- If I ask the same question twice, do I expect to receive the same answer?
- How much does it cost?
- Does my question require the LLM to read large transcripts?
I had intuition about the tradeoffs between each of these setups, but what was completely unknown to me was the size of the tradeoffs relative to each other.
- Worse coverage - but 5% worse or 50x worse?
- Cheaper - by a buck or by $200?
- Timing - 1 minute difference or an hour difference?
I decided to do it myself, the data-driven way, and publish everything as I go - partly out of curiosity, partly because I think the results are useful to anyone sitting on a pile of conversations.
One frozen set of 1,000 of our own customer calls. Five frozen questions. Every credible approach, run under identical rules, scored on the same four axes — coverage, consistency, cost, time — one post per approach over the coming weeks. The fifth axis, accuracy, waits for the final report — the answer key doesn't close until every system has run, so no approach (including ours) gets graded early.
And yes, at the end, Rippit takes the same exam. It will be run under the same frozen prompts and the same rules, so seven posts of results are on the record before Rippit gets a single number.
Nobody, including us, gets scored on accuracy until the answer key closes after every system has run. The final report is the full side-by-side.
This is Part 1: the setup everyone tries first.
Claude in the chat app, connected to your warehouse.









