by Jason Lemkin | Feb 17, 2026 | Blog Posts, Career Growth & Advice, Growth, Leadership, Marketing, Q&A, Sales |
Dear SaaStr: Is There Any “Con” In Giving Our Sales Tool For Free to Early-Stage Startups? Free can absolutely work. Done right, it’s built some of the biggest companies in B2B + AI: ChatGPT. Claude. Cursor. Slack. Zoom. Canva. Notion. Figma. Almost...
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 | 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 23, 2026 | Blog Posts, Career Growth & Advice, Growth, Product, Q&A |
Dear SaaStr: How Do You Sell B2B Products to Bigger Enterprise Customers? You solve their problems. Large enterprises use lots of tools, widgets, and pieces of software in their businesses, but they tend to use the obvious, trusted solutions. They aren’t looking for a...
by Jason Lemkin | Jan 18, 2026 | Blog Posts, Growth, Q&A |
Dear SaaStr: What Do The Top Sales Reps Do … That The Other 99% Don’t? I have a pretty good sense what the Top 10% do, though I’m not 100% sure about the top 1%. On the surface, they seem to be doing the same things the rest of the Top 10%...
by Jason Lemkin | Jan 15, 2026 | Artificial Intelligence (AI), Blog Posts, Growth, SaaStr.Ai
Ryan Anderson, CEO of Filevine, shared their AI transformation playbook at SaaStr AI London. Here’s the thing: their new AI revenue now exceeds their SaaS revenue on a quarter-over-quarter basis. This is the roadmap. The Filevine Story: 10 Years of Grinding,...
by Jason Lemkin | Jan 9, 2026 | Blog Posts, Fundraising, Growth, Q&A |
Dear SaaStr: How Do I Deal With Investors That are Unhappy With The Company? Be transparent. And show them an honest, data-driven path to a better future. First, investors get most upset when founders hide things. And founders tend to hide things more when times are...
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 | Dec 19, 2025 | Blog Posts, Growth, Hiring, Human Resources, Q&A |
Dear SaaStr: We Are Growing Too Fast to Handle the Workload, but We Can’t Afford to Hire New Employees. What’s wrong with our business model? Nothing. We’ve all been there. Almost all of us, at least. In SaaS, this typically happens somewhere between $3m...
by Jason Lemkin | Dec 4, 2025 | Blog Posts, Growth, Hiring, Sales, Sales |
A mistake many founders make is hiring a VP of Sales who has many strengths — but is not great at selling themselves per se. A VP of Sales who is smart, polished, and worked at the right place, in a management-level position. That can talk about quota...
by Jason Lemkin | Nov 26, 2025 | Blog Posts, Career Growth & Advice, Growth, Hiring, Product, Q&A |
Dear SaaStr: How Long Should a CEO Continue Being the Head of Product? Roughly — only for as long as it’s about a 10-hour a week job. Or often, maybe only up to $3m-$5m in ARR or so. These days, especially, I see way too many B2B companies at $8m-$10m ARR or beyond...
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...