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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
Right Now, We Run 4+ AI SDR Agents. Here’s Why.
We’ll take four A+ specialized AI agents over one B+ all-in-one platform every time. At least … for now. The all-in-one AI agent builders promise simplicity. What they deliver is mediocrity across every function. Every function. The demos look great. Production tells a different story. Here’s our stack today: Artisan for outbound. Three instances running…
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5 Interesting Things, Blog Posts, Scale
Entrata at $575m ARR Growing 23% Is First of the Next Wave of PE-Backed Software IPOs. The Catch: Almost None of Them Are Accelerating.
Entrata filed its S-1 on May 28 to list on the NYSE under the ticker “ENT.” It’s the multifamily property management Operating System out of Lehi, Utah, founded way back in 2003, with Silver Lake holding majority control since 2022. The numbers are solid but not jaw-dropping. $500m+ ARR, growing 23%, cash-flow positive. What does…
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Blog Posts, Early, Hiring
The Best Sales Execs Are Great at The Interview Process, Too
If a sales exec makes it anything but effortless to schedule a job interview with them, Basically it won't work out — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) February 13, 2024 So I remember years ago I went to hire my first VP ever. To make it even tougher, I’d never hired anyone for this role at…
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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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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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