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Databricks CRO Ron Gabrisko: 5 Interesting Learnings on Selling at a $190B AI Company: Flat SDR Headcount, 6-10% Reply Rates, and Free Seats That Unlocked Consumption
Ron Gabrisko joined Databricks as CRO when it was doing under $1M in ARR. Databricks is now a $190 billion company doing $7B+ ARR growing at a pace like we have never seen before. Ron sat down with Sam Blond, co-founder of Monaco and former CRO of Brex, on the SaaStr AI Podcast. They last…
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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai, Sales
10 Months Into AI for GTM That Actually Works: The CRO Matters More Than Ever. Every Other GTM Role Is in Flux.
We are about 10 months or so into AI for go-to-market that actually works: agents running real motions in production, booking real meetings and closing real dollars. In that time, agents have absorbed much of SDR, first-line support, a growing share of CS, and big parts of marketing ops and RevOps. Self-serve is closing deals…
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Blog Posts, Scale
The $300 Billion Software Debt Wall: The Big B2B Defaults Unfortunately Haven’t Even Started Yet
The big defaults for software debt … are unfortunately yet to come @wsj “Solera, a maker of software for vehicle maintenance, has about $8 billion in loans coming due in 2028 and 2029. Vista Equity Partners, which acquired the company in 2016, had planned an initial public… pic.twitter.com/E8NamhNAde — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) October 27,…
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Aaron Levie, CEO and Co-Founder of Box
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Schmoozing Is Dead, Agents Are Hitting 120% of Humans, and Growth Is the Only Thing That Matters: 10 Things From the Closing Q&A at SaaStr AI Annual 2026
We just wrapped SaaStr AI Annual 2026, and the closing Q&A on Day 3 ended up being one of the most engaged of the whole gathering. No script, no prepared deck, just an hour-and-a-half of questions from the audience on the topics most on their mind....
Dear SaaStr: What Was the Toughest Rejection You Ever Had in Sales?
Dear SaaStr: What Was the Toughest Rejection You Ever Had in Sales? The hardest rejection I’ve had in sales was around renewals. Especially ones I thought we really had earned. But still lost. In particular, in the early days of EchoSign / Adobe Sign, we had a...
Dear SaaStr: What Is the Playbook for a Successful Customer Success Team?
Dear SaaStr: What Is the Playbook for a Successful Customer Success Team? A good playbook for customer success is all about driving retention, expansion, and customer happiness while making it scalable: Hire Truly Product-Savvy Customer Success Managers at First Focus...
AI at Scale: 8 Learnings from monday.com Co-Founder and Co-Ceo Eran Zinman
monday.com Co-CEO and Co-Founder Eran Zinman recently sat down with SaaStr CEO and Founder Jason Lemkin to share his insights on their journey, including how they’ve leveraged AI, maintained growth, and expanded into multiple product lines.
The 2025 SaaS Vibe Check: What Founders Need to Know Right Now with SaaStr CEO and Founder Jason Lemkin
SaaStr CEO and Founder Jason Lemkin did a vibe check into the state of SaaS, AI, venture funding, and the rollercoaster of building a business in 2025.
Dear SaaStr: Can an Entrepreneur Back Out of a Signed Term Sheet Without Damaging Their Reputation?
Dear SaaStr: Can an entrepreneur back out of a signed term sheet without damaging their reputation? In my experience — Yes, probably. As a founder, you can back out of a term sheet if something is off, or even if you just get another offer you prefer. There is a lot...
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