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Blog Posts, Customer Success
Do You Treat Your 20-Year Customers Worse Than Your New Ones? You Probably Do
You probably do treat most of your oldest, longest lived customers far worse than a new prospect. As crazy as that sounds at some level. We’ve talked enough about our really, really rough experience with old, dated Adobe Marketo for marketing automation. They broke our unsubscribe link for weeks. Then they blamed us. Then they…
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Blog Posts, Sponsored Posts
Automate the Admin, Not the Relationship: How Reevo’s Agents Made Sellers 5x More Productive
A seller spends 70 to 80 percent of the day not selling. Research, meeting prep, note-taking, follow-ups, CRM updates. The job has looked the same for 25 years, and most of it is administrative work the rep is bad at and resents. That was the starting point for Reevo’s session at SaaStr AI 2026. Ali…
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Blog Posts
The Kindness Gap in VC Fundraising: Why a Little Grace Goes a Long Way
The fundraising process is brutal. We all know this. But here’s what I keep seeing that drives me crazy: VCs say: “We passed on that one.” Founders say: “We chose not to give them an allocation.” Look, I get it. Both sides are trying to maintain some dignity in what’s essentially a rejection process. But…
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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....
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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