Dylan Sellberg · Sr. Director of Product, Samsara · prev. HubSpot AI
I teach software
to do the work.
I led HubSpot’s flagship AI launches — ChatSpot, Breeze, and Breeze Agents, three straight years on the INBOUND main stage. Now I build the agent platform at Samsara, where AI rides shotgun with the people who keep the physical world running.
>shipping: AI agents for the physical economy @ samsara
03
Patents
Including one co-invented with Dharmesh Shah
03
Main-stage launches
INBOUND '23, '24, '25 — three years running
80+
AI features shipped
Unified into one platform: Breeze
73%
Fewer crashes
Reported by fleets on Samsara's AI safety tools
01 — The arc
From inboxes
to interstates.
Act I · HubSpot
Walked in an implementation specialist. Walked out the director who put HubSpot’s AI on stage.
I learned software from the inside — watching real businesses collide with real products — then spent my career closing that gap. Rebuilt the CRM data model. Shipped AI deduplication before “AI” was a pitch deck. Took the Facebook Messenger integration from zero to one. When the ChatGPT moment hit, I was leading product for HubSpot’s AI Innovation Labs — and we moved first.
- →ChatSpot — HubSpot's first AI assistant
- →Breeze — 80+ AI features, one coherent platform
- →Breeze Agents, Studio & Marketplace
- →3 patents — AI concierge, entity resolution, custom objects
Act II · Samsara
The digital economy has plenty of copilots. The physical economy is where AI gets real.
Trucks, fleets, job sites — the operations that feed, build, and move everything. At Samsara I lead product for the agent platform: AI that briefs a driver before the route, coaches them through it, and debriefs after, tracking 45+ risk factors the whole way. When this software does its job, someone gets home safe. That’s a product review I take personally.
- →Voice agents that coach drivers in real time
- →Personalized pre-trip briefings, at fleet scale
- →AI role-play & guided coaching for managers
- →Up to 73% fewer crashes for fleets using the AI safety stack
02 — Shipping log
Launched on stage.
Proven in production.
2023
ChatSpot
HubSpot's first AI assistant, launched into the ChatGPT spring
Shipped
2024
Breeze
One AI platform — Copilot, Agents, Intelligence
Shipped
2025
Breeze Agents
20+ digital teammates, plus Studio and a marketplace
Shipped
2026
Samsara agent platform
AI coaching that rides along with commercial drivers
In flight
03 — How I operate
Strong opinions,
shipped weekly.
01
Demos are promises.
If it can't survive contact with a real customer, it isn't a product — it's theater with a waitlist.
02
Agents earn trust like new hires.
Small tasks first. Receipts always. Autonomy is compensation for good work.
03
The model isn't the moat.
Everyone rents the same brains. The moat is the work you wire them into — the data, the context, the job to be done.
04
Speed is table stakes. Taste is the edge.
Anyone can ship an AI feature in a weekend now. Knowing which one not to ship is the job.
05
Build for the person doing the work.
Not the person buying the software. The driver, the rep, the human with a quota and a family.
04 — After hours
The building
doesn’t stop at five.
I’ve been building things since I was 11, and the habit stuck. These days that means arcade games for my son — the toughest stakeholder I’ve ever shipped for: instant feedback, zero diplomacy — a live market dashboard I check before breakfast, and this site, which an AI agent redesigned while I supervised. The tools changed. The itch didn’t.