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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai, Sales
Why You Don’t Want Humans Doing Outbound Anymore
Last week a sales rep at one of the leading public B2B software companies emailed me twice in 48 hours. The first email offered “insights” on buyer intent and AI efficiency … and shared none. It just listed their three product lines, and asked if I wanted to “benchmark” their software. The second email, sent…
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Blog Posts
When Growth Slows, Folks Start Wanting to Do the Crappy Things. Fight It.
So when growth slows, the conversations change. Especially from your CRO. When growth slows, the conversations change. Especially from your CRO. You start to hear: A ton of talk about raising prices. A lot. There are good reasons to raise prices. You added a lot of value, the market moved, you were underpriced from day…
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Blog Posts, Company Culture, Fundraising, Growth, Human Resources, Q&A
Dear SaaStr: Do VCs Want To Talk To Senior Execs That Quit a Portfolio Company?
Dear SaaStr: Do VCs Want To Talk To Senior Execs That Quit a Portfolio Company? Sort of. Maybe. Generally, if the issues are around: harassment or any inappropriate conduct, or fraud or misleading financials, etc, or something else that is wrong legally, ethically, morally, financially, etc. then I definitely need and want to have the…
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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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