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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
The SaaStr AI Guide to Building a Top-Tier Inbound AI Agent: 17,000 Conversations, ~600 Meetings Booked, and 60% More New Business
Our inbound AI agent has had 17,000 conversations with prospects in the last 12 months and booked about 600 meetings for SaaStr AI Annual 2026. And for 2027, it’s running almost 2x of the prior 12 months. Together with the newer self-serve agent we added on top of it, our inbound agents drove a 60%…
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Blog Posts, Hiring, Sales
Why It May Take You 12-18 Months to Hire a Great VP, Sales — Period. And What to Do About It.
We’ve talked a lot about hiring a VP, Sales. It’s just such a critical accelerate-or-decelerate decision for a post-Initial Traction SaaS company. We’ve talked about the 48 Different Types of VP Sales, What a VP Sales Really Does, and a Script to Use When Interviewing a VP Sales. But even armed with all that, I’ve gotta admit,…
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Blog Posts, Q&A
Dear SaaStr: Why Are Pricing Tiers So Effective?
Dear SaaStr: Why Are Pricing Tiers So Effective? I’m no pricing psychologist or true expert, but a few learnings: Buyers like a >few< choices. Not too many, but 1 or 2. It empowers them. In product marketing and sales, always give a buyer that is interested, but dragging her or his feet … choices. One…
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"SaaStr is the largest community of people who like enterprise software on the planet. It’s a great community of people trying to build companies and learn from one another. It’s pretty amazing to see."
Aaron Levie, CEO and Co-Founder of Box
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Eric Yuan, CEO & Co-Founder of Zoom
"SaaStr is the undisputed thought leader in how to build SaaS businesses. Jason is legendary."
Lew Cirne, CEO of NewRelic
"SaaStr is the undisputed thought leader in how to build SaaS businesses. Jason is legendary."
Lew Cirne, CEO of NewRelic
"SaaStr has pulled the entire SaaS community together in a powerful way."
Scott Dorsey, CEO of ExactTarget
"SaaStr is definitely the largest collection of people who like enterprise software — on the planet."
Aaron Levie, CEO and Co-Founder of Box
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Dharmesh Shah, CTO of Hubspot
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Popular Q&A
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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