Now our AI is making product recommendations Did not expect this A strong AI will do many things you did not expect pic.twitter.com/ARUg3jXoHr — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk) April 24, 2025 So our SaaStr AI is new but it’s already done over 30,000 (!) conversations with B2B executives.  In just its...
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Dear SaaStr: Is Bashing Your Competitors in Marketing OK? Yes, a few folks make this work.  Marc Benioff has made a career of bashing Oracle for years, Microsoft, and more.  Positioning them as very dated platforms, very aggressively.  I’ve also seen my own competitors do this effectively. When you look at how Copilot has been...
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So recently we had a SaaS buying experience that led to a No that is very common but many don’t realize is there, or at least is there that much: A SaaS Pricing Gap We went to buy Riverside, a podcasting tool, after years of being on Zoom.  We wanted to move to Riverside, it’s...
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So before we had AI, we had automation 😉 Of course, we still have plenty of automation.  So much of business software in the end is about automation.  But AI has begun to change everything here.  And before AI, RPA was revolutionary.  Robotic Process Automation.  Call it fancy scripts if you want, but UiPath is...
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Dear SaaStr: What Are Some Things We Can Do To Get Churned Customers Back? Reactivations are when previously churned customers come back and start paying again. Reactivations are way too often overlooked, but they can be a meaningful lever for growth if you approach them strategically.  Our B2C friends often obsess over there, but in...
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So averages (and medians) when it comes to start-ups can be a bit misleading.  After all start-ups are a business of trying to build an outlier. Still, the latest data from Carta is very helpful in illustrating an overall trend the gaps between venture rounds are getting longer and longer: Per Carta, the median time...
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The Strong Outbound, Crappy Follow Up.  It’s now new, but it’s accelerating with AI. It’s going to be a more and more common playbook in the Age of AI. Take last week. I got an incredible well timed, well written email from an agency about helping on production side of our podcast. And we do...
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Dear SaaStr: Besides Fast Growth, What Are VCs Looking For in Founders? In the end, most VCs are looking for huge market pull, and ultimately, massive growth first and foremost. But founders are > 50% of the bet, too. Investors evaluate startup founders based on a mix of personal traits, leadership potential, and their ability...
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SaaStr Annual 2025 is not just another SaaS event—it’s the largest gathering of SaaS, Cloud, and AI founders in the world, and this year, we’re taking it to the next level with the second year of our VIP Summits. These exclusive, role-specific gatherings are designed to bring together the best and brightest revenue and operational leaders...
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Dear SaaStr: What if I’m not sure that my VP Sales is the right person? 🤷‍♀️If you’re not sure your VP of Sales is the right person, you’re already in a tricky spot. The reality is, at the VP level, you can’t “fix” them if they’re not a fit. And that’s likely your fault for...
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