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Blog Posts, The Agents
The Agents Episode #005 is Out! Our 2 AI VPs Cost $257/Month, a Website Willed Itself Into Becoming an Agent, and QB Sent 83 Personalized Emails at 12:20am
Amelia and I just recorded Episode 005 of The Agents right before 2026 SaaStr AI Annual. You may have missed it in all the fun of the big event, here’s your chance to catch up! Most importantly: we both got the cost number completely wrong for our AI Agents. Our AI VP of Marketing (10K)…
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Blog Posts, Early, Marketing, Marketing, Metrics, Q&A
Dear SaaStr: As a Startup, What Are Some Effective Ways For an Underdog to Take Down Their Competition?
Dear SaaStr: As a Startup, What Are Some Effective Ways For an Underdog to Take Down Their Competition? It depends on the gap. In B2B historically, I’d argue if your competitor is larger than you, at $8M-$10M+ in ARR and growing quickly, with even reasonably happy customers, then it’s too late. Too late to “take…
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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
Even a Mediocre Prompt Can Build Pretty Good Software Today
Here’s the exact prompt I typed into Replit the other day “ok i have an idea where we built a new speaker card page, where if you upload a headshot, we build you a 1080×1080 card on a background you pick from (one is attached) and show your headshot and ‘I’ll Be at SaaStr AI…
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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
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Lew Cirne, CEO of NewRelic
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Lew Cirne, CEO of NewRelic
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Scott Dorsey, CEO of ExactTarget
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Aaron Levie, CEO and Co-Founder of Box
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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. We went off on...
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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