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...
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...
The Future of B2B Marketing is AI Agent Recommendations. And AI Agents Play Favorites.
It’s bigger than GEO. Bigger than SEO. This is about being the #1 answer when 700 million people ask AI what to buy. Replit says use @HubSpot. (Right or wrong) These are the battles you just have to win in 2026+ AI Agents Have Favorites. You Need To Be One Of...
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: 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...
CEO & Founder
Related Posts
