Dear SaaStr: How Long Does It Take the Average B2B Startup to “Exit”?
Dear SaaStr: How Long Does It Take the Average B2B Startup to “Exit”? I took a look a little while back at how long it took the average SaaS company that was sold for $1B+ to get that acquisition. The answer? 11.7 years on average, with a median of 10.0...
Your Marketing Site Should Be Even Better Than Your Product
When a new head of marketing joins a start-up and the first thing they want to do is “refresh the marketing site”, I always quietly groan a bit. Look, a marketing site is important. But don’t leads matter more? Shouldn’t improving the funnel...
What’s Your Loss Rate? You Really Should Know
Per @lightspeedvp survey of 154 venture-backed sales teams, the #1 reason deals don’t close is “no action”. And the #3 is “went silent”. These aren’t reasons. These are non-reasons. If you really want to know why, you have to push the team harder....
Dear SaaStr: What’s It Like to Have Your Company Acquired by One of the Tech Giants?
Dear SaaStr: What’s It Like to Have Your Company Acquired by One of the Tech Giants? It’s a lot of change. The pressure is mostly or at least partially off. Unless there is a huge earn-out or retention payment tied to performance, the pressure is off. Not all of...
In SaaS, The CEO Never Gets to Step Away From Sales
The biggest mistake you can make as a founder when you hire your first VP of Sales is stepping out of sales I see this again, and again It only works with the very best VPs of Sales Every other first VP of Sales needs you doing at least half of what you were doing...
Dear SaaStr: What’s the #1 Mistake New Sales Leaders Make?
Dear SaaStr: What’s the #1 Mistake New Sales Leaders Make? Let me just summarize my #1 observation here: the top mistake first-time sales managers make is recruiting. In that — they can’t do it. They can’t recruit great reps. They can recruit some mediocre...
Dear SaaStr: What Qualities Make a CEO The Best In Their Industry?
Dear SaaStr: What Qualities Make a CEO The Best In Their Industry? I’ve invested in 5 start-ups that had a $1,000,000,000+ cash exit or IPO. The CEOs were all quite different. Some extroverted, some introverted. Some wicked smart, some merely very smart. Some direct,...
You Have $100M ARR, 100%+ NRR, and 10,000 Customers. Why Are You Quitting to Start an AI Company?
Another founder I know—one running a company at $100M+ ARR—just announced on LinkedIn they were leaving. Stepping down. Handing over the keys. The reason? They were “excited to explore what AI could do in the space.” Everyone congratulated them in the...
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. And in 2026, more than ever. You’ll find 90% of the time you’ll want to not just tell a prospect who you are competing with, but do so aggressively. And box the competition...
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...
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