Keegan Otter works on AI strategy for HubSpot's Sales Hub, where he is helping build the next set of agents inside the CRM. Before HubSpot he was co-founder and CRO of Warmly, the person-level website intent and AI inbound agent company. He joined when it was four people and about $50K in revenue and helped take it to roughly $8M in ARR in a little over three years, ending with HubSpot acquiring the company in 2026. He has worked every seat in the revenue org, from SDR, starting his cold-calling career as a rep at Outreach, to RevOps director, VP of sales and CRO. He advises four early-stage startups and owns the Window Screen Guys in Arizona.
“If I hire an AE that makes 140, 150 in the SMB segment, they can't be touching deals less than 15 to 20K.”
“And a lot of people don't realize like, that's what it takes is taking a couple steps back to perfect the process to go 10 steps forward.”
“I made the joke that when I first came in, their meetings were with everyone's mothers and their grandmothers, 'cause I'm like, this title would never buy.”
“We don't need any more free design partners. We need customers.”
“Marketers don't wanna pick up their phones, right?”
“Don't be afraid to say what you do and what you're selling.”
“'Cause remember, sales is a losing statistic. The revenue game is a losing statistic, even in marketing.”
“And if you look at the history of Warmly's revenue growth, every quarter, we would resurface two to three deals that were previous closed-lost ops and be able to pull one to two as a closed-won.”