Been playing with @Rippling AI this week. Typed in: "I'm trying to plan an offsite for the team sometime in 2026. Suggest windows of times when the least amount of vacations are taken (based on historic data) and are spaced outside of national holidays and school holidays in the Bay Area." Got a bunch of windows, instantly, from live data. Software in the AI era is great!

@mamoonha @Rippling Where's the offsite?

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@mamoonha @Rippling The real flex isn't the prompt, it's that "historic data" actually existed and was clean enough to use. Most teams asking this question have vacation data scattered across three tools and a spreadsheet nobody updates. What did the output actually look like?

@mamoonha @Rippling This is the real unlock, not just generating content, but making decisions on top of live data Feels like software is moving from dashboards → operators More signals in today’s breakdown ↓ thevcinternfromx.substack.com/p/vc-intel-dai…

@mamoonha @Rippling The offsite query perfectly shows what AI-native software means — not a chatbot wrapper, but natural language over live operational data with context awareness across multiple calendars. That used to take a data analyst an hour. Now it's a sentence.

@mamoonha @parkerconrad @Rippling Need it to do more. Location recommendations based on attendees, group hotel bookings, suggested flights, etc. All of the data is there to power the reasoning

@mamoonha @Rippling This is actually a pretty good idea

@mamoonha @Rippling That's killer. Essentially a custom LLM fine-tuned on your own company's HR data... the possibilities are endless.

@mamoonha @Rippling Give me a few windows and I’ll tell you where demand is actually lowest. 🫡

@mamoonha @Rippling Rippling AI's differentiator is that it queries Rippling's permissioned data layer (object graph) to retrieve results, allowing it to provide data-backed insights into your company. Without the data layer, the system wouldn't be able to answer using historical data

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@mamoonha @Rippling Now just need a hook into 7 rooms / OpenTable.

@mamoonha @Rippling Rippling is justifying it's name 🎉

@mamoonha @Rippling ❤️next step would be to book the flights in the same chat!

@mamoonha @Rippling parker's been cookin

@mamoonha @Rippling game changer!

@mamoonha @Rippling Trusted data. Genuine answer. Action taken. #RipplingAI