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 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...
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:...
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...
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