by Jason Lemkin | Mar 26, 2026 | Artificial Intelligence (AI), Blog Posts, Customer Success, SaaStr.Ai
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...
by Jason Lemkin | Feb 9, 2026 | Customer Success, Growth, Hiring, Leadership, Q&A |
Dear SaaStr: How Do We Close Bigger Deals? If you already have a few bigger deals under your belt, but most are smaller … a few higher-level suggestions: #1. Hire a Very Good VP of Sales that has sold at your “high end” price point. They will be much better at you...
by Jason Lemkin | Feb 2, 2026 | Blog Posts, Customer Success, Early, Marketing, Q&A |
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...
by Jason Lemkin | Jan 29, 2026 | Blog Posts, Customer Success, Growth, Q&A, SaaS Product Pricing, Sales |
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...
by Jason Lemkin | Jan 28, 2026 | Blog Posts, Customer Success, Growth, Marketing, Q&A, Sales, Sales |
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...
by Jason Lemkin | Jan 25, 2026 | Blog Posts, Customer Success, Marketing, Marketing, Q&A |
Dear SaaStr: My Customer Missed the Deadline for AutoRenewal. How Do I Handle This Situation? You can ask them to pay, for sure. But if they don’t want to, just turn the product off if they don’t pay. Then, Let it go and Move On. At a practical level, it is...
by Jason Lemkin | Jan 17, 2026 | Blog Posts, Customer Success, Early, Q&A, Sales |
Dear SaaStr: Should We Pay Our Sales Reps on Renewals? Simple answer: most don’t. You can, especially in the early days. But very few SaaS companies pay sales reps on renewals as they scale. And you can definitely pay on upsells and account expansion. Longer...
by Jason Lemkin | Jan 5, 2026 | Blog Posts, Career Growth & Advice, Customer Success, Customer Success, Growth, Q&A |
Hopefully, 100% of your customers love you. But as time goes on, you’ll oversell a few deals. Or not quite deliver in some fashion. Or fail to deploy in others. And some customers will ask for their money back. When they e-signed binding, good old-fashioned...
by Jason Lemkin | Jan 4, 2026 | Blog Posts, Career Growth & Advice, Customer Success, Customer Success, Growth, Q&A |
Dear SaaStr: What Were Aspects of Your Startup That Were Easier Than Anticipated? The part I didn’t originally get as a first-time B2B founder was how relatively easy it is to grow exising accounts and account size if your customers are happy. 120% NRR: Your revenue...
by Jason Lemkin | Jan 3, 2026 | Blog Posts, Career Growth & Advice, Customer Success, Customer Success, Growth, Q&A |
Dear SaaStr: What Do You Do With Churned Customers? You put them into a Get Them Back bucket and re-market to them with a dedicated program. And you have sales especially follow-up twice. Once in about 90 days, to see if they might want to come back —...
by Jason Lemkin | Jan 2, 2026 | Blog Posts, Customer Success, Marketing, Q&A |
Dear SaaStr: Should We Drop Customers That Complain Too Much? Sometimes, yes. But just as often, the ones that complain are the ones that care. And oftentimes, their complaints help focus you on the gaps you really do need to fix. One thing most SaaS companies get...
by Jason Lemkin | Nov 22, 2025 | Blog Posts, Customer Success, Growth, Marketing, Marketing, Q&A |
Dear SaaStr: What Types of Customers Should be Avoided and How Do I Recognize Them? You will get lots of advice on “bad customers”, “firing customers”, and the like. For the most part, in SaaS, I don’t agree. The “Bad Customer” Myth: Why Your Most...
by Jason Lemkin | Nov 18, 2025 | Blog Posts, Customer Success, Early, Leadership, Marketing, Q&A |
Dear SaaStr: How Did You Get Your First Major Customers? Secret here: every story is different. In my first start-up, it was pure hustle. We had a concentrated number of high dollar customers, so I did “outbound”. I found the right decision makers, got on the phone,...
by Jason Lemkin | Nov 14, 2025 | Blog Posts, Career Growth & Advice, Customer Success, Early, Leadership, Q&A |
Dear SaaStr: Is It Ridiculous To Call Yourself the CEO When Your Startup is Tiny? I used to feel that way, at least a bit. I used to look at tiny little startups and wince when a founder went around talking about himself as “CEO”. But then I had to learn how to Sell...
by Jason Lemkin | Sep 15, 2025 | Blog Posts, Customer Success, Customer Success |
It took me a little while to see activation rates as literally one of the 3-4 most important metrics in SaaS, but it probably is. I started to track activation rates at a lot of start-ups I work with, and I saw numbers that shocked me. I often see 60% or so...