Dear SaaStr: Does A Founder Need To Sell Themselves in the Early Days? Yes, a startup founder should absolutely handle sales when first getting started. It’s not optional—it’s critical. Here’s why: 1. You Need to Prove You Can Sell It If you can’t sell your product...
So I’ve wondered if more CEOs are stepping down. It’s sure felt like it. Recently we’ve seen the CEOs of Asana, Discord, Twilio, Instacart and Ironclad step down, among others. It felt like a trend, but I wasn’t sure. Well, the Wall Street Journal has the data. ...
So the great “AI Upsell” in SaaS and B2B may be over before it’s really truly begun. As AI began to take off in B2B, many rushed to charge substantially more for their “AI” — on top of already high per seat prices. But even as they...
Dear SaaStr: How Do I Become a VP of Sales Within 18 Months? The very best folks I’ve ever worked with have done it in 5 years. From new rep to VP of Sales. That’s the fastest. More on why here: 5-6 Years Is About As Fast As You Can Mint a True VP of...
Ok about 2,000 of you have already picked your 2025 SaaStr Annual + AI Summit sessions so far and here are the top sessions … for now: 1. The New Rules of SaaS Growth: What’s Next for AI, PLG, and Revenue Scale with HubSpot’s CEO 2. From Startup to $10B+:...
"The AI Slow Roll is Killing B2B Companies" – cost of AI is just an excuse– can't be just experimenting now– hard to shake out of your inertia with @rodriscoll + @HarryStebbings pic.twitter.com/eHliUamSx9 — Jason ✨👾SaaStr.Ai✨...
Dear SaaStr: Why Do Enterprise Customers Insist on Pilots? I know your sales team probably hates pilots, because in a sense, it means they have to sell the deal twice. Once for the pilot, and again to convert the pilot for a longer deal. Having an “opt...
Top Posts: #1. 10 Ways AI Will Change Sales Forever. It’s Already Happening, In Fact. #2. The #1 Thing That Makes Enterprise Customers See Value: A Great Dashboard #3. 20VC + SaaStr: The Hidden Game of Silicon Valley: Decoding Venture Capital’s New Rules #4. The...
Dear SaaStr: How will Ai Change Sales in The Next 12 Months? Within a year, an AI sales rep will join every human sales rep on every Zoom and call 🤖 95% of “I don’t knows” and “Uh I’ll get back to you” will be gone Within a year, an AI BDR will answer all inbound...
SaaStr Annual has always been the go-to event for SaaS founders, executives, and investors, but 2025 is shaping up to be the best one yet. Here’s why this year’s event is bigger, bolder, and more impactful than ever. It’s 50% about the intersection of AI + B2B,...
