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Datadog Stock Is Up +66%. Here Are 5 Reasons Why, And Why It’s the Cleanest AI Beneficiary in B2B.
Guess Whose Stock Is Up +66% year-to-date? And trades at 20x ARR? In the midst of the most challenging run for software stocks … ever? Datadog. As of May 22, 2026: $222.32 per share, +66.20% year-to-date. Market cap: $79B. 52-week low was $98.01 just months ago. 52-week high is right now. Why? They’ve leaned into…
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Blog Posts, Scale
Dropbox Hit $1B Faster Than Any B2B Company Ever. But Now, It’s The End of an Era
An end of an era Of my generation of SaaS CEOs, no star burned brighter than Dropbox It grew to $1B ARR faster than any before, and burning almost nothing, perfecting the PLG motion. The startup we all wished we founded. But in the end, there was no second act even pre-AI.… https://t.co/96BycqNq82 — Jason…
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Blog Posts, Early, Sales, Sales
That First Magical Sales Rep. The AI Era Edition.
A while back on LinkedIn and Twitter we had over 200,000 views and engagements on a quick post on “The Magical Sales Rep”, and another 500+ likes on a follow-up. It’s worth a deeper dive. Especially now in 2026, where the role of that first rep has shifted in the Age of AI. And is…
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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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