Dear SaaStr: Should Your Ask a Prospect What Competitors They Are Looking At?
Dear SaaStr: Should Your Ask a Prospect What Competitors They Are Looking At? Yes. You’ll find 90% of the time you’ll want to not just tell a client who you are competing with — but do so aggressively. And box the competition out at the start. “Great to learn about...
The 2x ARR Club: Don’t Let It Be You
There’s a new club in B2B nobody wants to join. It was there before, this club, but it’s gotten even more members since the SaaS Crash of 2026. A growing cohort of public B2B companies — not one or two, but twelve or more — are trading below 2.5x revenue....
Five “Cons” To Adding a Free Edition
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...
Dear SaaStr: How Do We Close Bigger Deals?
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...
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...
Dear SaaStr: How Do You Sell B2B Products to Bigger Enterprise Customers?
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...
Dear SaaStr: What Do The Top 1% of Sales Reps Do … That The Other 99% Don’t?
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%...
How Filevine Went from SaaS to AI-Native at $200M+ ARR — And Now Makes More Revenue from AI Than SaaS (A Roadmap for the Rest of Us)
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,...
Dear SaaStr: How Do I Deal With Investors That are Unhappy With The Company?
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...
What To Do When A Customer Wants to Cancel A Contract
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...
Dear SaaStr: What Were Aspects of Your Startup That Were Easier Than Anticipated?
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...
Dear SaaStr: What Do You Do With Churned Customers?
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 —...
Dear SaaStr: We Are Growing Too Fast to Handle the Workload, but We Can’t Afford to Hire New Employees. Help!
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...
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