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 B2B at least, I’ll give you a few metrics that are fairly reliable. The classic one still works, but in 2026 you need to layer in some new signals too....
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...
Dear SaaStr: How Do I Convince My CEO that Marketing is Important?
Dear SaaStr: How do I Convince My CEO that Marketing is Important? A lot of CEOs these days do seem to be late to truly invest in B2B marketing, and most especially, to hiring a true VP of Marketing. In the Age of AI, so many CEOs hack it to $5m, $8m, $20m+ in ARR...
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...
Dear SaaStr: How Big Should The Addressable Market Be to Go into Vertical SaaS?
Dear SaaStr: How Big Should The Addressable Market Be to Go into Vertical SaaS? To win in Vertical SaaS: – Can you charge at least $10k a year?– Can you add enough value to hit 110%+ NRR?– Can you get to 60% market share? If so, in many markets,...
Dear SaaStr: When Do You Start to Develop a Brand in SaaS?
Dear SaaStr: When Do You Start to Develop a Brand in SaaS? In my experience, probably as early as $2m worth of happy customers. At least the beginnings of a “mini brand”. At that point, you don’t have a world-famous brand or anything. But you do start to have a...
Dear SaaStr: Should We Over-Charge or Under-Charge our First Customers?
Dear SaaStr: Should We Over-Charge or Under-Charge our First Customers? My general rules: Overcharge if the customer is big, i.e., >$50k-$100k a year o nor so in ACV. Undercharge if the customer is smaller by revenue. There’s a method to the seeming madness...
If Times Are Tough — Don’t Hide. Be Present.
What I see CEOs at struggling start-ups do: – Go dark– Hide– Lash out– Tweet about lots of things non-work– Invest time on tiny expenses– Argue internally What should do: – Be Present– Be Honest– Be the Rock–...
Dear SaaStr: How Should I Present The Competition Slide of My Pitch Deck if I Have Too Many Competitors?
Dear SaaStr: How Should I Present The Competition Slide of My Pitch Deck if I Have Too Many Competitors? Simple Answer: Just pick the Top 5 competitors, that’s enough. Not just by revenue, but also, by significance. Longer Answer: The competitor slide is a chance to:...
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...
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