Customer.io's CEO built a Slack bot that audits every new strategy doc against the company's 20 to 50 ratified documents.
They call it Chiefy.
Here's the problem it solves. Every company has a corpus of "official" docs. The operating model, the strategy, the pricing philosophy. Then someone publishes something new, gets alignment, and three months later half of those docs quietly disagree with each other.
Nobody catches it because nobody has time to re-read two dozen documents every time one changes. That's why Notion goes stale.
Chiefy runs the audit automatically. Two use cases:
You create something new, like an analysis or a pricing doc. Run it through Chiefy and it flags discrepancies against the ratified corpus before it goes to other execs.
You ship something new and it IS the new direction. Chiefy tells you which older docs now need updating. "8 of these 12 disagree with this. Intentional or not?"
That second question is the killer feature. Recency bias means leaders contradict their own published strategy without realizing it. A bot that asks "did you mean to change the strategy or did you forget what it says" is an accountability check most leadership teams have never had.
Matthew Wensing, VP of Product at Customer.io, walked through Chiefy plus his full weekly stack in this episode: an analysis bot wired to Snowflake he's 215 replies deep with, and a scanner that reads dozens of Slack channels to find conversations where a PM should be involved but isn't.
A 400-person fully remote async company generates more threads than any human can read. They stopped pretending someone could.
Aakash Gupta (@aakashgupta)
This guy literally broke down how to use AI and NOT produce slop:
0:00 AI is a test
3:53 The 5am presentation
5:10 Never click "enhance"
6:19 Inventory before prompting
7:27 Dumping transcripts in
12:14 Matrix multiplication trick
13:50 Slides first, script second
15:08 Claude, the eager junior
17:04 "Stop suggesting next steps"
17:36 200 iterations beat one
17:53 Slop = micro hallucinations
18:44 Don't microwave output
19:02 The biology metaphor
20:20 Hide your real goal
22:05 When AI asks back
23:21 The game night rule
24:41 Layer complexity slowly
26:08 Reveal purpose last
27:29 Stress test the model
31:57 The unicorn name mistake
33:35 Claude confesses its weakness
38:48 Executives smell slop
40:56 The full weekly stack
43:05 The Slack scanner
45:06 The doc auditing bot
Video
— https://nitter.net/aakashgupta/status/2064476248596738543#m