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10 of The Top Mistakes First Time Founders Make. Again and Again and Again.
Dear SaaStr: What Are 10 of The Top Mistakes First Time Founders Make? Almost all entrepreneurs often fall into predictable traps. We make the same mistakes, again and again 🙂 Here are some critical mistakes they make and how to avoid them: #1. Underestimating the Time to Build a Viable Business Many founders think they’ll…
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Blog Posts, Growth, Leadership, Q&A
6 Key Signs a VP of Sales Can’t Scale Beyond $5m-$10m ARR
The best VPs can recruit in ways I barely understand You need someone for a key role? They somehow have 2-3 strong candidates in a week or two This is so, so hard But the very best VPs make it somehow look almost effortless It's also the only way to scale — Jason ✨👾SaaStr.Ai✨ Lemkin…
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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
Artisan’s Ava 2.0: What a Fully Autonomous AI BDR Actually Looks Like in Production with CEO Jaspar Carmichael-Jack
Most of the AI SDR pitches you hear sound the same. A founder gets on stage, shows a slick demo, and promises the death of the BDR. Then you ask one hard question and the whole thing falls apart. Jaspar Carmichael-Jack, founder and CEO of Artisan, did the opposite at SaaStr AI Annual. He ran…
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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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