12 Things You’ll Look Back On in B2B … And Regret
A little ways back on LinkedIn and Twitter, I put together a list of things that later, once you are successful, even very successful, you’ll regret. It got a lot of engagement from the B2B veterans out there, so I thought it would be worth digging in more on...
In The Early Days, You Won’t Have Enough Customers. But Your Mini-Brand Will Come to Your Rescue.
"You think brand doesn't matter in the early days. But it turns out, you'll have a 'mini-brand' far earlier than you might think. Often by just $2-$3m ARR. Customers in your niche, in the part of the market where you do win, will start to hear...
You’ll Lose Customers. It Hurts. But Don’t Let Them Become Angry Ex-Customers.
"If a customer wants to go, let them. In fact, help them. First, it really doesn't matter when they go, if they go. They drop off your ARR eventually. Second, treat them right, they may well come back." pic.twitter.com/QrDVkLyd19 — Jason...
Should You Visit More Of Your Prospects In Person? Almost Certainly
I remember the first customer I lost due to not showing up in person. They were a Fortune 50 customer. We did a CSAT survey, and every user loved us. The implementation was flawless. There were zero issues. And … we lost them at renewal. Our buyer was kind...
Got 100 Customers? Believe It Or Not, It’s Time for Your First User Conference
When I was figuring out B2B as a CEO for the first time, the last thing I wanted to do was a Customer / User Conference. I understood the importance of events like Dreamforce. Salesforce is a complex product, with (sometimes) long deployment cycles, professional...
Dear SaaStr: Does It Make Sense to Have Post-Sales Functions Report into Sales?
Dear SaaStr: Does It Make Sense to Have Post-Sales Functions Report into Sales? In many ways, this is the question of the day. So many SaaS companies, faced with slower growth, are moving CS in particular in to the sales department, trying to get more growth from the...
Lovable, Harvey & Assembly AI: How the Fastest AI Companies Rebuilt Customer Success. And Why NPS and Activity Scores Are Dead
The Forward Deployed / Customer Success track at SaaStr AI 2026 turned into something closer to an autopsy and a rebirth at the same time. Leaders from the fastest-growing companies in B2B + AI got on stage and said versions of the same thing: the post-sales playbook...
What Lovable, Harvey & Assembly AI Are Doing in Customer Success. That You’re Not
The fastest-growing companies in B2B + AI are not running the customer success playbook the rest of the market spent a decade building. At the FDE / CS Summit at SaaStr AI Annual 2026, leaders from the companies setting the pace got specific about what they’ve...
High NRR is Magic. It Can Also Hide a Lot of Problems.
Having high net revenue / dollar retention is the magic of B2B. If you have 120% NRR, you double in less than 5 years, even with no new customers. Above that, you really get into magical compounding growth. But here’s the 2026 reality check: high NRR has gotten...
Why It’s Year 3 When You Lose Your Larger Customers (And in The AI Age, It’s Becoming Year 2)
Recently I was catching up with a good friend who used to be CEO of an enterprise-y B2B social networking company. The usage and engagement numbers of his business were just awful. Customers bought because they thought their organizations needed this functionality,...
Our AI Customer Success Agent Is Working Harder Than 95% of Human CSMs I’ve Worked With. Maybe More Than 95%.
Here’s what happened yesterday. At 8:37am, our AI Customer Success “QBee” agent sent out 150+ personalized sponsor update emails for SaaStr AI Annual 2026. Not a batch blast. Not a mail merge with a first-name token. Every single email was genuinely...
Dear SaaStr: How Many Of Our Prospects and Customers Should I Meet Face-to-Face?
Dear SaaStr: Should an early- stage B2B startup meet every customer face-to-face to receive feedback? If you could — all of them. The more customers you meet in person, the more that buy from you, and the more “more stuff” they buy from you after,. The full data here...
Dear SaaStr: How Do You Change the Price of Your SaaS Product Without Upsetting Existing Customers?
Raise prices on existing customers,Doesn’t help if you are growing quickly. Just makes them unhappy. Raise prices on new customers,Forces you to deliver more value. Often makes everyone more happy. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) April 7, 2022 Dear...
Dear SaaStr: What Are Some Best Practices for Selling a New Product Into Existing Customers?
Dear SaaStr: What are some best practices for selling a new product/service to your existing SaaS clients? First, make sure your NPS is high. And drive it even higher. Here’s the bottom line: if your NPS is say > 40 or so, a significant portion of your customers...
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