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10 of The Toughest Lessons in Building a B2B Startup. Or Any Startup.
Dear SaaStr: What Were Some of the Toughest Lessons You Learned About How to Build a Successful B2B Business? Some of the toughest lessons I’ve learned … and continue to re-learn: Even very talented co-founders may leave. You need to also make sure they are 110% committed. More here. Very mediocre VPs and CXOs are…
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Blog Posts
Dear SaaStr: How Do You Become Successful at Enterprise Sales? What Are the Biggest Challenges People Experience?
If you haven’t done enterprise sales yourself before, the biggest thing to understand: you can do it. But, you’re going to have to hustle. Really hustle. Many founders want the customers and leads and users to come to them. They want to focus then on the funnel, A/B testing, optimization, SEO, SEM, etc. etc. That’s…
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Artificial Intelligence (AI), Blog Posts
Our Agents Never Picked Canva. 10 Learnings on Agent Pricing, Getting Picked, and Security From This Week’s “The Agents” With Ulrik Lehrskov-Schmidt
Amelia and I both canceled Canva this week. I’d been a customer for about 12 years. We weren’t angry at it, and nobody sat down and decided to replace it. Our agents just never had a use for it. That happened the same week Canva restructured 22% of the company. Melanie Perkins said in her…
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“We learned B2B pricing from SaaStr AI.”
Arsalan Tavakoli, Co-Founder & SVP, Databricks
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Marc Benioff, Founder, Chair & CEO, Salesforce
“Important learning opportunity. Could be transformative for your business / career.”
Amjad Masad, Founder & CEO, Replit
“We learned how to scale from SaaStr AI Annual. I was in the audience.”
Eran Zinman, Co-CEO, monday.com
“SaaStr AI is my peeps. It’s where us founders hang out.”
Dharmesh Shah, Co-Founder & CTO, HubSpot
“I tell every founder to read SaaStr AI. And come to SaaStr AI.”
Michelle Zatlyn, Co-Founder & COO, Cloudflare
“SaaStr AI is the only place where you can get this level of density of B2B founders.”
Aaron Levie, Co-Founder & CEO, Box
“SaaStr AI Annual is the Super Bowl of B2B.”
Eric Yuan, Founder & CEO, Zoom
Popular Videos
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Popular Q&A
7+ Tips On How To Build Your First Sales Team. When You Have Zero Experience Building One.
Dear SaaStr: How do you structure a sales team ... when you’ve got zero experience doing sales? Well, first go get some experience with sales. 🙂 At least, close the first 10 customers yourself. If you don’t, you’ll never have any idea how to do it. And the odds your...
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.
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