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Why AI SDRs Take 2 Weeks to Deploy. And Why Most People Still Prefer Chat.
Two lessons we’ve learned the hard way running AI agents across sales, marketing, and customer success at SaaStr in 2026. If you’re rolling out your first AI SDR, internalize these now. They will save you a lot of frustration. Lesson #1: Budget at Least 2 Weeks of Ramp Time. Always. Regardless of vendor. Regardless of…
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Blog Posts
Who Got the Most Leads at SaaStr AI Annual 2026? The Top 15 Tell You Exactly Where B2B Budget Is Going
We just wrapped SaaStr AI 2026, and the sponsor engagement leaderboard is in. It measures the one thing a sponsor actually cares about: how many leads they pulled from 10,000+ B2B + AI founders, operators, and buyers on the floor. Here’s the full top 15 by engagement: Replit — 1,423 leads (Vibe Coding / AI…
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Blog Posts, Exit
Why “No” in M&A Usually Means “No Forever”
“Time kills deals.” Everyone says it. It is especially true in M&A. On 20VC x SaaStr a little ways back, we were discussing OpenAI’s acquisition of TBPN. The outreach happened in January. Fidji was new as head of apps, thought it would elevate OpenAI’s brand, pitched it internally, and got the green light. It took…
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Aaron Levie, CEO and Co-Founder of Box
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Eric Yuan, CEO & Co-Founder of Zoom
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Lew Cirne, CEO of NewRelic
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Lew Cirne, CEO of NewRelic
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Scott Dorsey, CEO of ExactTarget
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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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