by Jason Lemkin | Nov 21, 2025 | Blog Posts, First $100m ARR, Scale
Ramp just announced it has crossed a stunning $1B ARR — growing 100% (!) and just closed its latest VC round at a $32B valuation. Co-founder CTO Karim Atiyah came to SaaStr Annual + AI Summit to share how they scaled to the first $100m ARR. And see everyone at...
by Jason Lemkin | Nov 21, 2025 | Blog Posts, Growth, Hiring, Human Resources, Q&A |
Dear SaaStr: What Were The First Five Hires You Made After Product-Market Fit? My first 5 hires at Adobe Sign / EchoSign, beyond the core founding+ team, once we had paying customers and first, if early, product-marketing fit: #1: Full-time sales rep at $8k-ish MRR....
by Jason Lemkin | Nov 20, 2025 | Blog Posts
We’re back with another episode of 20VC x SaaStr, and this week we’re diving into the deals and market dynamics that are reshaping venture capital as we know it: Cursor just raised $2.3 billion at a $29.3 billion valuation with less than 100 or so...
by Jason Lemkin | Nov 20, 2025 | Artificial Intelligence (AI), Blog Posts, Marketing, SaaStr.Ai, Sales
After deploying 5 AI SDRs across inbound, outbound, and follow-up—here’s the actual numbers, unexpected learnings, and what it really takes to make them work Six months ago, we had essentially zero AI SDRs at SaaStr. Today, we’re running five specialized...
by Jason Lemkin | Nov 20, 2025 | Early
The data is in. And it’s remarkable. And it’s what we’ve all been feeling and seeing in venture. The Unicorns Really Are Back. Back to The Highest Level In 3+ Years. October 2025 just became the biggest month for unicorn creation in over three...
by Jason Lemkin | Nov 20, 2025 | Blog Posts, Early, Q&A |
Dear SaaStr: How Many More Junior Marketers Should you Hire Before Hiring a VP of Marketing? Unlike many positions, I say 0 if possible. In fact, one of the 10 most unforced errors I see founders make is hire someone too junior to get marketing going. If you are,...
by Jason Lemkin | Nov 19, 2025 | Blog Posts, Leadership
I’ve seen it again and again across 30+ investments, 10+ unicorns, and hundreds of portfolio company board meetings. There’s one pattern that predicts VP failure better than anything else I’ve seen. Not their resume. Not their pedigree. Not even...
by Jason Lemkin | Nov 19, 2025 | 5 Interesting Things, Blog Posts, Scale
So Valve isn’t a B2B company per se, but it has evolved from a gaming platform to an epic marketplace (Steam) with unit economics that are almost unprecented. I still think we can learn fro it. Valve will generate over $17 Billion in total gross revenue and $4...
by Jason Lemkin | Nov 19, 2025 | Growth, Marketing, Q&A, Sales, Sales |
Dear SaaStr: Our sales team has a 7% win rate over last 6 months. CEO has put full revenue accountability on the marketing team. How do I keep sales from failing? Not to be too much of a Pollyanna — but a 7% win rate isn’t necessarily all bad. In fact, if you have an...
by Jason Lemkin | Nov 18, 2025 | Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
Cursor just crossed $1B in ARR less than 24 months from launch. And just closed a $2.3 billion Series D at a stunning $29.3 billion valuation. For a company that launched its product … 17 months ago. This isn’t just another funding announcement. This is...
