I flew back to India from Boston for a few weeks this year, and I’m still processing everything that came out of it. Five sessions, three cities, roughly 600 people — and one thread running through all of it: people weren’t looking for answers about AI. They were looking for someone to think alongside.
Bengaluru: the room that didn’t want to leave
At the Datadog Summit in Bengaluru, I spent four hours with 120+ engineers and technology leaders on GenAI and LLM monitoring. It wasn’t a lecture — more a working session, hands on keyboards, real problems on the table.
The part that stayed with me happened after the session ended. People lingered. They wanted to think through their own AI architectures out loud, right there in the room. Those hallway conversations were the whole point of flying halfway around the world.
On stage at AWS Summit, Bengaluru
A different kind of room: 300+ people, C-suite down to platform engineers, and me on stage talking about monitoring GenAI applications — going beyond the traditional golden signals.
Afterward, people tracked down our booth. Not for a pitch. Just to keep talking. That kind of energy isn’t something you can manufacture with slides.
Kochi: an hour that maybe shifted something
In Kochi, hosted by the ITLC Kochi community, I spent a full hour with 100+ IT leaders from across South India. We started with observability and found our way to GenAI. For a lot of people in that room, it was their first real introduction to Datadog.
Walking out of that one, knowing you might have shifted how a group of leaders thinks about something — that’s a feeling that’s hard to put into words, and I’m not going to try much harder than that here.
The two quieter rooms
Not every moment on this trip was a stage or a packed hall. Two of the ones that mattered most were much smaller.
In Delhi..
I pulled up a chair with our Enterprise Sales team. No slides — just a real conversation about GenAI fundamentals, and how to walk into a C-suite discovery call with actual confidence instead of a script.
And, In Bengaluru..
A different table, a different team — Mid-Market Sales this time — for a candid session on competitive positioning. How to read a deal. Who to actually talk to. When to walk away.
Both of those conversations kept going long after the session was supposed to end. That’s usually the sign you hit on something real.
What I keep coming back to
GenAI is moving fast, and the teams shipping it need to see inside what they’ve built — traces, cost, latency, model behavior, all of it. That’s the exact problem I get to work on at Datadog, and this trip was a reminder of why I like being in this space.
Grateful for every one of those hours. Now — back to Boston, and back to work.