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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
Vertical B2B Leader Owner Acclerated After $100M ARR With Agents. The Key Insight: Every Time a Customer Logs In, Owner Has Failed.
Everyone agrees you have to build with AI now. That argument is over. The unsettled questions are what a product built on agents is supposed to measure, and what stops a foundation model from doing to you next quarter what you just did to your own category. Adam Guild has been running that experiment at…
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5 Interesting Things, Blog Posts, Scale
5 Interesting Learnings from Atlassian at $6.6 Billion in ARR: 28% Growth, 44% RPO Growth, and a 35% One-Day Stock Pop
Atlassian closed its fiscal year on June 30 and reported on August 6. Going in, it was one of the most doubted names in enterprise software. The bear case was simple: AI agents write the code, AI agents file the tickets, and the tools that track the work get squeezed out of the middle. The…
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Blog Posts, Customer Success, Growth, Sales
9 Tips To Closing More Bigger Deals
If you already have a few bigger deals under your belt, but most are smaller … and you want to build on that and close more “bigger” / enterprise deals … a few higher-level suggestions: Hire a Very Good CRO / VP of Sales that has sold at your “high end” price point. She will…
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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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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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