by Jason Lemkin | Aug 19, 2026 | Blog Posts, Customer Success, Growth, Sales |
If you already have a few bigger deals under your belt, but most are smaller … and you want to build on that and close more “bigger” / enterprise deals … a few higher-level suggestions: Hire a Very Good CRO / VP of Sales that has sold at your “high...
by Jason Lemkin | Jul 13, 2026 | Blog Posts, Customer Success, Customer Success, Sales |
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...
by Jason Lemkin | Jul 8, 2026 | Blog Posts, Customer Success, Sales
The Discount That Would’ve Kept Us So we’re going to churn off Adobe Marketo. The irony: I was one of the first 10 Marketo customers. Ever. I’ve been a customer (with a break) for goodness, the better part of two decades. And a reference account for...
by Jason Lemkin | Jun 15, 2026 | Blog Posts, Customer Success
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...
by Jason Lemkin | May 14, 2026 | Blog Posts, Customer Success
In some ways, we helped build the Customer Success category at SaaStr a generation or so ago. Some of the earliest writing here on Second Order Revenueand the power of a funded, dedicated CS organization informed a generation of B2B founders. We believed in it deeply....
by Jason Lemkin | Jan 30, 2026 | Artificial Intelligence (AI), Blog Posts, Customer Success, SaaStr.Ai
Think about how customers bought enterprise software in 2019. Or even in 2023. You’d get sold by a sales rep. Then you’d hire an Accenture or other third party to deploy it over 9-12 months. And you’d hope and pray it worked like the sales rep...
by Jason Lemkin | Jan 5, 2026 | Blog Posts, Career Growth & Advice, Customer Success, Customer Success, Growth, Q&A |
"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...
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 1, 2026 | Blog Posts, Customer Success, Early, Q&A, Sales |
Dear SaaStr: What’s The Best Way to Get Traction After We Have A Few Paying Customers? Answer: try everything that just might work, even a little bit. Then: double down on anything that works even a little. That may sound obvious, but what I mean is, most start-ups...
by Jason Lemkin | Dec 17, 2025 | Blog Posts, Customer Success, Early, Marketing, Q&A |
Dear SaaStr: What Do You Do When Your Startup is Not Growing Anymore? First, be honest about why. You can blame it on macro issues if you want, or on the competition over promising, or whatever — but if growth has radically decelerated, it’s likely because you...
by Jason Lemkin | Dec 2, 2025 | Artificial Intelligence (AI), Blog Posts, Customer Success, SaaStr.Ai
Recently I reached out to support at 2 fintechs we used, both at $500m+ ARR, and what did support say? “We’ll get back to you in a day.” There’s no excuse for this anymore in the Age of AI. There was no excuse ever, but pre-AI, keeping up...
by Jason Lemkin | Nov 26, 2025 | Artificial Intelligence (AI), Blog Posts, Customer Success, SaaStr.Ai
Dear SaaStr: We’re thinking about deploying AI for customer support. Is it actually good enough yet, or should we wait? Don’t wait. Do it now. Pick a leader and go. Just don’t forget to train it. You have to train AI support with your real data, FAQs,...
by Jason Lemkin | Nov 10, 2025 | Artificial Intelligence (AI), Blog Posts, Customer Success, SaaStr.Ai, Scale
Vanessa Gatihi joined OpenAI as their first customer success hire 18 months ago. Today, she leads a global CS team as Head of AI Deployment & Adoption spanning San Francisco, New York, Munich, Paris, Dublin, London, Singapore, and Korea, serving a thriving...
by Jason Lemkin | Oct 30, 2025 | Blog Posts, Customer Success |
Dear SaaStr: What Should My New VP of Customer Success Be Doing In The First 30-60-90 Days? Here’s how I’d structure their 30-60-90 day plan to ensure they’re focused on the right priorities: First 30 Days: Meeting With Customers — ASAP. And Deep Dive and...