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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
The “Buyers Won’t Trust an AI” Objection Is Already Collapsing
The most common pushback we hear when talking about AI account executives replacing human AEs goes something like this: “Buyers won’t trust an AI. They only buy from humans they trust.” I understand the intuition. In theory, it sounds reasonable. In practice, very few deals over Zoom actually build that much trust. If any. And…
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Blog Posts, Q&A
Dear SaaStr: Should I Use an AI SDR Before I Have a Working Human SDR motion?
Dear SaaStr: Should I Use an AI SDR Before I Have a Working Human SDR motion? No. This is the single biggest mistake I see across all company stages, from $1M ARR startups to multi-billion-dollar public companies, and it will sink your AI SDR deployment. The Core Problem If outbound doesn’t work with humans, buying…
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Blog Posts, Fundraising
You Have All the Power as a Hot AI Founder. Just Don’t Accidentally Push VCs Into “Maybe Not.”
If you’re building a hot AI startup right now, you have the leverage with VCs. Full stop. There are the best of times for you, if you have traction and a true agentic product. VCs are fighting to get into the best AI deals. Rounds are closing in days. Valuations are eye-popping. And founders are…
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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 Videos
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Popular Q&A
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...
How To Reverse-Engineer a $100M Exit: SaaStr on My First Million Pod
How do you reverse-engineer your first million as a SaaS startup founder? SaaStr founder and CEO Jason Lemkin chats with Sam Parr on the popular YouTube channel and podcast My First Million about what’s required to make it on the map for a $100M exit and then reverse engineers the steps to get there.
Rule 1: New minimum is $400K per employee
Rule 2: Go multi-product
Rule 3: Your second product must be bigger than your first product
Cheat code: Double your prices
Rule 4: 30% of your revenue is international
Rule 5: Localize your product
Cheat code: Remove friction
Rule 6: 100% net revenue retention
Rule 7: Don’t raise double digit millions
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