A tale of two new SaaStr AI tools that reveals the future of enterprise AI economics We just shipped two new AI-powered tools at SaaStr, and the LLM costs and token usage patterns tell a bimodal story about where enterprise AI costs are headed. Both SaaStr AI tools...
It's totally OK to ask a VC at the end of a pitch meeting, "Based on what you know now, what are the odds you'd invest?" In fact, it can save a lot of time — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) September 8, 2025 It’s totally OK to ask a...
Dear SaaStr: We are at $10MM ARR and it’s … hell. We can’t seem to breakthrough and we are short on cash. Do we sell? Push through? Last year we grew 40% so growth is slow but we’re still growing. We all get burnt out in a scenario like this. ...
Would you hire every VP on your team if you had to do it over again? If not, you know what you have to do Be Kind But get going — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) May 28, 2025 The Hardest Question Every CEO Must Answer: Would You Hire Every VP on Your Team...
Dear SaaStr: What Are The Two Most Important Marketing KPIs on The Way to $10m ARR? For an early-stage SaaS business at $3M ARR driving to $10m ARR, the two most critical marketing KPIs to track are Pipeline Contribution* and Customer Acquisition Cost (CAC) Payback...
Last week marked the busiest IPO stretch since 2021. Six companies raised $4.4 billion in five days. But is this the sustainable comeback founders and VCs have been waiting for, or just another false dawn? The IPO window isn’t just cracking open—it’s...
It took me a little while to see activation rates as literally one of the 3-4 most important metrics in SaaS, but it probably is. I started to track activation rates at a lot of start-ups I work with, and I saw numbers that shocked me. I often see 60% or so...
Dear SaaStr: What’s the Best Way to Help Top SDRs Become SMB Account Execs? The best way to prepare a top-performing SDR for an SMB AE role is to give them a structured path that builds on their strengths while exposing them to the full sales cycle. And most of...
This week one of our favorite founders at SaaStr, Jeff Lawson founding CEO of $15B+ Twilio, joined the 20VC x SaaStr pod live with Harry Stebbings, Jason Lemkin, and Rory O’Driscoll. Jeff Lawson built Twilio from zero to IPO and beyond, navigating the...
An early investment I made, I met with the CEO of a public company that wanted to buy them for $50m The startup hadn’t raised much, they said No Years later, they sold for almost $1B The founders made about the same they would have, years earlier, in the first deal...
