The walls are closing in on data silos. The rise of ChatGPT as the front-end to our AI world is pushing them to open. And legacy B2B and SaaS vendors are about to learn a painful lesson about who really owns customer data. Albeit not without some battles. Fight it...
Eventually … everyone goes a bit enterprise Eventually … everyone adds a sales team https://t.co/6h3LesrvRo — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) October 16, 2025 The lure of freemium (like The Force) is strong. No headaches. Customers try and...
Dear SaaStr: How Do I Hire a Great First 1-2 Sales Reps? Hiring your first AE (Account Executive) is a pivotal moment for your startup. It’s not just about finding someone who can sell—it’s about finding someone who can sell your product in the messy, unstructured...
Why 40% Cloud Adoption Marks the End of Easy Growth. And why the AI budget war is just getting started Top 5 Takeaways 1. The 40% Tipping Point: With 40% of workloads now in the cloud, SaaS has hit market maturity. The easy growth is over—companies like Zoom...
If you’re feeling relieved you finally got that great VP to join the company, read this from @jasonlk next. (And if you are that VP, definitely read it first.) https://t.co/cVodwksp3N — James Cham (@jamescham) July 23, 2022 I’ve now worked with or invested...
This chart from Altimeter Capital tells one of the most dramatic stories in software history. Google took 15 years to reach 1.2 trillion annual searches. That catapulted it into the $2 Trillion leader it is today. ChatGPT? It hit 1 billion searches per day in under a...
Dear SaaStr: How Do You Balance Optimism with Realism When Pitching VCs? Successful startups balance optimism with realism by presenting a compelling vision while grounding their projections in credible, data-backed assumptions. Bear in mind, most VCs — not all,...
I see it happening everywhere. Board meetings where someone inevitably asks, “Don’t we need a VP of AI?” I saw a term sheet the other day where a leading VC firm reserved $1m of the round … for hiring a “VP of AI”. Leadership teams...
Dear SaaStr: What are the most common mistakes founders make hiring their first real sales teams? A few key mistakes I see start-ups making > 50% of the time: Hiring Early Reps (#1 – #3) That You Personally Wouldn’t Buy From. Don’t hire someone with the...
Andreesen Horowitz recently pulled some great data from the deals its invested in and looked at. Now this isn’t all start-ups, it’s many of the best ones. But the data is telling. What “Working” Means in the Era of AI Apps: The New Enterprise...
