Dear SaaStr: My Customer Missed the Deadline for AutoRenewal. How Do I Handle This Situation?
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...
If AI GTM Tools Were Half as Good As Cursor or Replit, It Would Be a Different World Today. They Will Get There.
We’ve been running AI GTM agents for almost a year now. We use Artisan for outbound, Qualified (now Salesforce) for inbound, Agentforce for Salesforce-native outreach, Delphi for Digital Jason. We’ve sent 20,000+ AI messages and generated over $2M in...
Dear SaaStr: A Big Tech Co Launched a Competitive Product. How Can I Tell How Serious They Are About It?
Dear SaaStr: A Big Tech Co Launched a Competitive Product. How Can I Tell How Serious They Are About It? In SaaS at least, I’ll give you one metric that is fairly reliable: How many dedicated sales and GTM professional do they have, just 100% selling the competitive...
Dear SaaStr: How Do I Compete with a Company that has Unlimited Capital — and I Don’t?
Dear SaaStr: How Do I Compete with a Company that has Unlimited Capital — and I Don’t? First, does your highly-funded competitor have a dominant brand yet? If not, it may not matter. There is no “winner” yet. The #1 brand trumps capital. But if they have...
Dear SaaStr: What Do You Do When Your Startup is Not Growing Anymore?
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...
Dear SaaStr: What Types of Customers Should be Avoided and How Do I Recognize Them?
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...
6 Months of AI SDRs: What’s Worked, How They Brought In $1M+ in 90 Days, and the Real Data Everyone’s Asking For
After deploying 5 AI SDRs across inbound, outbound, and follow-up—here’s the actual numbers, unexpected learnings, and what it really takes to make them work Six months ago, we had essentially zero AI SDRs at SaaStr. Today, we’re running five specialized...
Dear SaaStr: Our Sales Team Has a 7% Win Rate. Are We Failing?
Dear SaaStr: Our sales team has a 7% win rate over last 6 months. CEO has put full revenue accountability on the marketing team. How do I keep sales from failing? Not to be too much of a Pollyanna — but a 7% win rate isn’t necessarily all bad. In fact, if you have an...
Dear SaaStr: How Did You Get Your First Major Customers?
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,...
The GTM Playbook for Building a $300M+ ARR Business: Lessons from ClickUp’s COO Gaurav Agarwal
How to scale from startup to $300,000,000+ ARR by mastering the fundamentals of go-to-market strategy Building a billion-dollar B2B business isn’t about finding secret hacks or silver bullets. They don’t last or scale. It’s about mastering...
The AI Marketing Revolution: Key Insights from G2’s CMO on How B2B Buying Has Forever Changed
From the new SaaStr “Swapping Notes” podcast series – essential listening for every B2B founder and marketing leader navigating the AI transformation The AI Marketing Revolution: Key Insights from G2’s CMO on How B2B Buying Has Forever Changed...
10 Things My VP of Marketing Did — and Didn’t — Do in Their First 30 Days
So one of the classic SaaStr posts we update and is even more true than ever: ask every VP you hire, especially your VP of Marketing, what they most want to do. Have them make a list. And then realistically, they will only do the first 3-4. They may do a little of...
Yes Customer Testimonials — Done Right — Are Super Important
Do customer testimonials really matter in the age of AI? They still do. Maybe even more so. They are incredibly important. We spend so much time marketing and selling to customers. And building stuff for them. But almost no one thinks enough about what a buyer...
The Confounding Logic of Discounting
There can be nothing more frustrating in the middle-early days than when sales closes some great deal for, say, $125,000 a year … but you “knew” they could have gotten $200,000 if they just held the line on discounting. You’d talked to that...
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