by Jason Lemkin | Apr 15, 2026 | Blog Posts, Early, Q&A |
Dear SaaStr: I’ve Been Out of Sales For 6+ Years. Is It Too Late to Get Back In? I stayed at home as a parent and then played professional poker for several years. Ok here’s the thing: you have 2 flags already (and staying home for the kids isn’t...
by Jason Lemkin | Apr 14, 2026 | Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
We were in a Waymo heading to SFO to get to Coachella. About 25 minutes to the terminal. And I had this idea rattling around: what if every SaaStr AI Annual 2026 attendee could generate a custom “I’ll Be There” card for LinkedIn — with their own...
by Jason Lemkin | Apr 14, 2026 | Artificial Intelligence (AI), SaaStr.Ai
Anthropic just hit $30 billion in annualized revenue. $30 billion. In a company founded in 2021. With somewhere between 3,000 and 5,000 employees, depending on which source you trust. That is the not just the fastest $30 billion revenue run in the history of...
by Jason Lemkin | Apr 14, 2026 | Blog Posts, Career Growth & Advice, Early, Leadership, Marketing, Sales |
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–...
by Jason Lemkin | Apr 14, 2026 | Blog Posts, Early, Q&A |
Dear SaaStr: What are some benefits you can add to get people to buy a product besides discounts and add-ons? You can help them actually deploy your app. To actually, truly get the value out of it. Not just buy it. Buying a product is just Step 1, at best. Mediocre...
by Jason Lemkin | Apr 13, 2026 | Blog Posts
We’re doing it again. For the 4th year running, we’re hosting the SaaStr AI CMO Summit as part of SaaStr AI Annual 2026 — a half-day deep dive exclusively for the best marketers and GTM executives operating at the cutting edge of AI + B2B. And this year,...
by Jason Lemkin | Apr 13, 2026 | Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
Everyone rolling out AI Agents at scale is saying the same thing right now: we can’t hire enough forward deployed engineers. And they’re right. But most companies are drawing the wrong conclusion from that fact. The shortage of FDEs isn’t just a...
by Jason Lemkin | Apr 13, 2026 | Blog Posts, Career Growth & Advice, Early, Hiring, Q&A, Sales, Sales |
Dear SaaStr: What’s the #1 Most Important Thing To Look For In Your First Sales Rep? The #1 most important criterion for your first 2 reps is: would you buy from her? For real? Would you truly, 100%, buy your own product from them? 98% of the reps you interview …...
by Jason Lemkin | Apr 12, 2026 | Blog Posts
Every year at SaaStr AI Annual, some of the best conversations I have are with Fellowship attendees. Not because they’re the most senior people in the room. But because they bring perspectives that the rest of us just don’t have enough of in B2B. We...
by Jason Lemkin | Apr 12, 2026 | Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
I’ve been a happy, paying Canva customer for 8+ years. I genuinely love the product. It’s affordable. It just works. The team at SaaStr still uses it regularly. The founders are iconic leaders we all look up to. And yet … I’m thinking about...
