SaaS-focused media and events company founded by Jason Lemkin.
“Raise it once and let it go... It's not your company. It is not your cap table.”
Source→“I think there's a geopolitical issue around who has the sort of strategic control of the world. That is a different issue from, should we use a model that was trained in China.”
Source→“Its AI VP of Revenue proposed mirroring the system of record into a $5 Postgres instance.”
“an analysis of 22,000 attendees found that 49.7% of executives had changed jobs within 16 months.”
“New agent-access charges from Salesforce, Atlassian, and HubSpot could make automated API usage expensive, with one estimate putting SaaStr's annual bill at $240,000 for 35,000 to 40,000 daily calls.”
“I was with Jason Lemkin yesterday from SaaStr, who's as AI pilled as they can be. And he's like, honestly, it's not better than the others.”
Source→“Having a subject matter go in and answer 20 questions about a disease, about history... The amount of power you can get in a domain by having a subject matter answer just 20 or 30 questions, right? Five minutes, 10 minutes. The amount of power you can add versus the generic LLMs... it's a step function.”
Source→“I had two of my fastest growing portfolio companies saying they already blew through their budget this year... None of my slowest growing companies have said that.”
Source→“Participants: Harry Stebbings (Host), Jason Lemkin (SaaStr founder/investor), Rory O'Driscoll (Scale Venture Partners)”
Source→“If there is efficiency gains from AI across R&D and sales and marketing in particular, everyone's going to be doing 20% layoff just because it's 20% more efficient. My aha is this discussion and the last discussion are, in fact, the same discussion.”
Source→“54% of new enterprise logos came through a fully self-serve funnel (real ACV, real terms, real invoicing) without an AE, using Clay and Claude for qualification and Intercom Fin to guide the buyer journey.”
“Jason Lemkin at SaaStr shared how Anthropic rebuilt its commercial sales org from scratch in January 2026.”
“We pay more for Salesforce than we used to... We're down to a couple seats on Salesforce per se, right? Because our team is 20 agents, three humans. But we pay more for Salesforce than we used to.”
Source→“Aaron Levy was on Harry Stebbins 20VC this week and said there's going to be a whole new category of $500K to $1M new year jobs for operators over the coming years.”
Source→“The parking pass system took 90 minutes to build and eliminated hundreds of hours of annual labor.”
Source→“Agent Mail — YC-backed company providing pre-warmed email infrastructure for autonomous AI agent outbound. Jason discovered it via Claude recommendation, set it up in one minute, got immediate high deliverability to inbox.”
Source→“Qualified — AI-powered pipeline generation platform (Salesforce-native). Used by SaaStr for both sales and customer success routing. Cited as one of their best-performing autonomous sales agents.”
Source→“"Having a chatbot on your website is not a replacement for actually fixing the problem... having that does not — that should not exclude you from actually backfilling support, from finding FDEs, from finding folks that know the product." — Amelia Lerutte [00:58:35]”
Source→“"It basically did everything short of hitting the send button... our AI VP of marketing, much like a true — true things I used to do as our VP of marketing, would segment the list, write the copy, identify the right folks. But also, he came up with this campaign." — Amelia Lerutte [00:05:42]”
Source→“We're down to a couple seats on Salesforce per se, right? Because our team is 20 agents, three humans.”
Source→“Our AI sales team are third-party tools. We use Artisan, Qualified, Monaco, and Agent Force, right? Those are four. For the most part, those do run autonomously if we set them up, review the text, review the guardrails. They have then sent over 100,000 emails on their own.”
Source→“You've got to look at the DAUs and MAUs and WAUs. You've got to in the stealth churn area because if you're feeling all confident because your product's cheap so people don't... But look at those DAUs and WAUs because our DAUs and WAUs and MAUs are zero for Notion.”
Source→“Jason is someone who wants to work with a very lean team. He's doing more than when he had people on staff.”
Source→AI-extracted from podcast / newsletter / paper summaries. May contain errors.