by Jason Lemkin | Oct 17, 2025 | Blog Posts, Q&A |
Dear SaaStr: What is the Most Typical Career Path to VP Sales in a B2B SaaS Company? The most typical career path to becoming a VP of Sales in a B2B SaaS company usually involves a steady progression through sales roles, gaining experience at each level while...
by Jason Lemkin | Oct 16, 2025 | Blog Posts
We’re back with another deep dive into the shifting landscape of venture capital, and this week we’re joined by a legend who’s seen it all—Roger Ehrenberg. Roger founded IA Ventures in 2008, building one of the most respected early-stage portfolios...
by Jason Lemkin | Oct 16, 2025 | Blog Posts, Sales |
As start-ups get bigger and bigger, leads get distributed more and more ratably — to an extent. Start-ups often move to round robin to distribute leads, then they segment them, and then sometimes territories even now. Should You Round-Robin Leads? Or Make Reps...
by Jason Lemkin | Oct 16, 2025 | Blog Posts, Q&A |
Dear SaaStr: What’s a Good Lead-to-Demo Ratio for our SDR:AE Handoff? We have a mid-market sale. Lead-to-demo rate is another critical metric to track, especially for outbound teams. It measures the percentage of leads your team engages with that actually convert...
by Jason Lemkin | Oct 15, 2025 | Blog Posts |
So a little ways back Harry Stebbings and I did a deep dive on how to build your first sales team. A lot of it was great, some of it needed a refresh, so I updated it and edited it to bring it into 2025. It’s a great quick 20+ minute deep dive on many top...
by Jason Lemkin | Oct 15, 2025 | Blog Posts, Q&A |
Dear SaaStr: I’m Joining as VP of Sales at $3m ARR. What Should My Priorities Be? Here’s how I’d prioritize week 1 as a new VP of Sales at a $3M ARR SaaS startup. At this stage, you’re small enough to move fast but big enough that the stakes are real. The goal is to...
by Jason Lemkin | Oct 14, 2025 | Artificial Intelligence (AI), SaaStr.Ai
So there has never been a “start-up” like OpenAI. Already with 800,000,000+ users and a breathtaking $500 Billion (!) valuation. But it’s also raised and spent epic amounts. So as the chart from FT below shows — all the historic investors...
by Jason Lemkin | Oct 14, 2025 | Blog Posts |
If you ever think “Should I fire this person?” even once—fire them kindly, but … well … now. This is going to be controversial. But hear me out. I used to think you should give people the benefit of the doubt. Coach them. Give them another...
by Jason Lemkin | Oct 14, 2025 | Blog Posts
Anique Drumright, VP of Product for IT at Rippling, shared how Rippling does it at SaaStr Annual + AI Summit. And see everyone at SaaStr AI 2026 on May 12-14 in SF Bay!! Most B2B companies follow the same playbook: Build one product. Perfect it. Scale it. Move slowly...
by Jason Lemkin | Oct 14, 2025 | Blog Posts, Q&A |
Dear SaaStr: How Many Calls Can an Enterprise AE Self-Source Per Week? The 50+ calls per day for a many SDRs still holds. But it doesn’t really work for an enterprise AE trying to generate a material portion of their pipeline themselves in large accounts. For...
