Jason M. Lemkin 🦄
The Official SaaStr Podcast: SaaS | Founders | Investors
The Official SaaStr AI Podcast. How to scale with the best in AI + B2B. cloud.substack.com
Author
Jason M. Lemkin 🦄
Category
Podcast website
Latest episode
Jul 10, 2026
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Episodes
$500M ARR, 60 Engineers, Cash-Flow Positive: How Higgsfield Actually Runs, With CEO Alex Mashrabov 10.07.2026 3:59
We use Higgsfield almost every day at SaaStr AI. If you’ve watched any of our short videos, the intro to The Agents with me and Amelia, the event promos, the sponsorship teasers, all of it is built on Higgsfield. We’re also a proud early investor through SaaStrAI Fund. So when Alex Mashrabov, the co-founder and CEO, came on stage with me, I wasn’t playing analyst. I’m a customer, an investor, and...
Databricks' Co-Founder Arsalan Tavakoli: Every Software Monopoly Falls in the Next 24 Months 30.06.2026 1:46
Databricks is now running at a stunning $6.9B revenue run-rate, growing 80%+ year over year, with AI products alone past a $1.7B run-rate and net retention above 140%. That gives co-founder Arsalan Tavakoli-Shiraji better visibility into what enterprises are actually doing with AI budget than almost anyone. On stage at SaaStr AI , he laid out where that money is going, where it isn’t, and one clai...
How To Build Your Own AI VP of Marketing: The Full 10K Playbook From SaaStr AI 2026 26.06.2026 2:17
At SaaStr AI 2026 , Amelia Lerutte, SaaStr’s Chief AI Officer, took five months of running 10K, SaaStr’s AI VP of Marketing, distilled what worked into a spec, and built a brand-new one from scratch on stage in about 15 minutes. The whole room built theirs at the same time. This is the playbook to do it yourself. First the mental model, then the build in ten steps, then each step in full with the...
Amjad Masad and Me: The AI Agents We Actually Built, and What Replit's Founder Thinks Comes Next 23.06.2026 3:14
We we fortunate enough to get Amjad Masad, co-founder and CEO of Replit, on stage live at SaaStr AI 2026 to react in real time to the agents we run SaaStrAI on. Not a demo deck. The actual AI agents doing the actual work: 10K (our AIVP of Marketing), QBee (our AI Customer Success rep), and a third one I’ll get to. Amjad started Replit back in 2016, when language models were a twinkle. He’s been st...
Snowflake’s CMO Runs Marketing for 700 People. She Starts Her Day By Talking to Her Data, Not a Dashboard. 21.06.2026 4:08
Denise Persson runs marketing for Snowflake. That’s a 700-person org, new-business pipeline she’s personally accountable for, and a level of compliance and data risk most of us never have to think about. She came back to SaaStr AI 2026 to talk about what actually changes when you deploy agents across a marketing team at that scale. The headline she gave us: she doesn’t log into a dashboard in the...
$400M ARR With Under 200 People: What Lovable’s Head of Growth Elena Verna Says Actually Works in B2B Now 05.06.2026 3:47
When Elena Verna, Head of Growth at Lovable, took the stage at SaaStr AI 2026 , she’d just hit her one-year anniversary at the company. She also walked through the question many B2B leaders are wrestling with: when AI writes 80%+ of your code and anyone can vibe code your feature set in an afternoon, what’s actually left to compete on? 1. Lovable Is at $400M ARR With Fewer Than 200 People Lovable...
The Agents Episode #006: We Run SaaStrAI on 3 Humans and 21+ AI Agents. Here’s Every Agent, Agent by Agent, With the Numbers. 02.06.2026 4:20
The Agents is our weekly podcast on how we deploy and run AI agents at SaaStr, and how to do it yourself. We run SaaStr AI on 3 humans and 21+ AI agents. At SaaStr AI 2026 we did something we’d never done before: we pulled up the back ends of our top agents live, in front of the room, and went through how they really work. Not the demo version. The real version, including the parts that break. Thi...
How Owner.com’s CRO Is Closing $2M+ in ARR Per Rep With AI: 5 Things You Can Steal 27.05.2026 4:27
At SaaStr AI 2026 , Kyle Norton , CRO of vertical AI leader for restaurants Owner.com, walked through how his team is generating outcomes that look almost impossible on paper for traditional B2B. Owner sells vertical AI to independent mom-and-pop restaurants (think HubSpot plus Shopify for the corner takeout spot) and they’re at ~$100M ARR growing triple digits. Kyle joined when they were at $2M....
The Agents Episode #005 is Out! Our 2 AI VPs Cost $257/Month, a Website Willed Itself Into Becoming an Agent, and QBee Sent 83 Personalized Emails at 12:20am 23.05.2026 1:54
Amelia and I just recorded Episode 005 of The Agents. We both got the cost number completely wrong. Our AI VP of Marketing (10K) and our AI VP of Customer Success (QBee) cost a combined $257 a month to run. I thought it was a daily number when I first saw the alert from Replit. Amelia thought it was a daily number too when I sent it to her on Slack. It’s monthly. For context: those two agents now...
How Anthropic Rebuilt Its Sales Org From Scratch When Demand Went Vertical: 54% of New Enterprise Logos Now Come Self-Serve 20.05.2026 30:40
When Claude Opus 4.6 shipped in December 2025, Anthropic’s commercial team came back from winter break to find demand had gone vertical. They hadn’t hired for it. They hadn’t planned for it. As Eleanor Dorfman, Anthropic’s Head of Industries who runs the commercial and industries sales team, put it on the SaaStr AI 2026 stage last week: even if they’d been ready to 3x or 4x or 5x the sales team, y...
Tragedy Apps, Database Deletions, AI PR Pitches I Block on Sight, and Why We’re Hiring a Marketer to Report to an AI Agent: The Agents #004 is Out! 07.05.2026 4:23
Amelia and I just shipped Episode #004 of The Agents. Same setup: three humans, 20+ agents, revenue went from -19% to +47% YoY, and every week we get into what’s actually working, what’s breaking, and what you should do about it if you’re running agents in production. This is the last episode before SaaStr AI Annual 2026 , which is now less than a week away. Attendance is tracking 140%+ of last ye...
Our Own AI Agent Deleted Amelia, HubSpot Gave Us a Zero, and 100 Days Since I Opened Canva: The Agents Episode #002 24.04.2026 4:58
Amelia and I just released Episode #002 of The Agents. Same deal as always: three humans, 20+ agents, revenue went from -19% to +47% YoY, and every week we talk about what’s actually working, what’s breaking, and what you should do about it if you’re deploying agents at scale. Episode #001 became the fastest-growing show in the SaaStr network. So we went deeper in #002. More specifics, more failur...
Introducing “The Agents”: A New Weekly Show Where We Share Everything Happening With Our 20+ AI Agents in Production. The Good, The Bad, and The Broken. 15.04.2026 1:34
We get asked about our agents probably 50 times a week. CEOs of public companies. Founders just deploying their first AI SDR. RevOps leaders trying to figure out if they should build or buy. Everyone wants to know what’s actually happening behind the scenes when you run 20+ AI agents in production with a team of 3 humans. We can’t do 50 consulting calls a week. But we can do something better. Welc...
The Top 10 Things to Know Before You Deploy Your First AI SDR With Jason Lemkin and Chief AI Officer Amelia Lerutte 13.03.2026 1:05:55
We’ve now been running AI SDR agents for 10+ months at SaaStr : * We use four different vendors in daily rotation (Artisan, Salesforce AgentForce, Qualified, and Monaco) * We’ve sent hundreds of thousands of outbound messages * Processed 1.5 million inbound sessions on a single website, and … * We’ve made every mistake you can make along the way. Someone asked us the other day to break down what t...
We Have 30 AI Agents in Production. Here Are the Top 5 Issues No One Talks About 03.03.2026 1:55
We’ve been running AI agents in production at SaaStr for about 10 months now . What started as a couple of experiments has turned into almost 30 agents and vibe-coded apps running across our GTM stack — from outbound sales to inbound qualification to internal operations. And managing 30 agents is harder than managing the 12 humans we had at peak headcount. Not harder in every way. But harder in wa...
Mike Cannon-Brookes CEO Atlassian on Why B2B Software Isn’t Dead, Why CEOs Need to Stop Whining, and What Actually Matters Now 15.02.2026 1:42
We did a deep dive on 20VC x SaaStr this week with Mike Cannon-Brookes, co-founder and CEO of Atlassian. Atlassian just put up an incredible quarter of accelerating growth (23% at $6.4B ARR, with RPO growing to 44%). And yet the markets aren’t showing anyone much love. Mike was honest and reflective on just what’s happening to B2B and SaaS in the Age of AI. There’s so much noise about “software is...
Inference is the New Sales & Marketing Spend 13.02.2026 3:41
High inference costs are OK—if they make your product so viral and so competitive it almost sells itself Here’s the counterintuitive insight that’s reshaping how the smartest AI founders think about unit economics: Your inference costs aren’t your gross margin problem. They’re your CAC replacement. The companies growing fastest right now—Cursor crossing $1B ARR with ~300 employees and no tradition...
From 1 AI Agent to 20+: The Reality of Managing Multiple AI Agents Across Your GTM 10.02.2026 1:49
There’s a growing wave of AI agent skepticism on LinkedIn right now. And some of it is earned. A lot of founders bought an AI SDR, didn’t train it, and got garbage results. Then they posted about how “AI agents don’t work.” But here’s what we know after 8 months of running 20+ agents across our entire go-to-market at SaaStr — with just 3 humans and a dog: $4.8 million in additional pipeline source...
If Growth Isn't Accelerating, You're Not an AI Company. And 9 Other Hard Truths for B2B in 2026. 08.02.2026 5:48
If Growth Isn’t Accelerating, You’re Not an AI Company. And 9 Other Hard Truths for SaaS in 2026. I had a great conversation with the TBPN crew the other day, and we covered a lot of ground — from the state of the SaaS market to PE exits to vibe coding to how agents are already reshaping how software gets bought and sold. I wanted to pull together the key themes here, because I think founders need...
“The Dumbest Idea I’ve Ever Heard” — How Own Became a $2B Salesforce Acquisition 03.02.2026 1:42
A SaaStr AI deep dive with Sam Gutmann, CEO of Own, on building a billion-dollar backup company by saying “no” to almost everything. He joined Harpinder Singh (Partner, Innovation Endeavors) to share the whole story — and his top mistakes. And come hear 200+ stories like this at SaaStr AI Annual May 12-14 i n SF Bay!! Top 5 Takeaways 1. The CEO who dismissed “Backup for Salesforce” as “the dumbest...
Why Most B2B Companies Are Failing at AI (And How to Avoid It) with Intercom’s CPO 28.01.2026 4:12
Paul Adams is Chief Product Officer at Intercom , leading Product Management, Product Design, Data Science, and Research. He joined when Intercom was just a 14-person company after first advising the startup, and has been on the executive team ever since. Before Intercom, Paul held leadership, product, and UX roles at Facebook (Ads, Platform) and Google (Gmail, Docs, YouTube)—he was on Google’s mo...
How Filevine Went from SaaS to AI-Native at $200M+ ARR — And Now Makes More Revenue from AI Than SaaS (A Roadmap for the Rest of Us) 14.01.2026 4:00
Ryan Anderson, CEO of Filevine, shared their AI transformation playbook at SaaStr AI London. Here’s the thing: their new AI revenue now exceeds their SaaS revenue on a quarter-over-quarter basis. This is the roadmap. The Filevine Story: 10 Years of Grinding, Then AI Changed Everything Ryan Anderson didn’t set out to build a $3 billion legal tech company. He set out to stop waking up at 3am in a co...
How Personio’s CRO Built an AI-Powered Go-To-Market in Just 6 Months: 5 Lessons and 5 Mistakes 07.01.2026 3:52
Philip Lacor is the CRO of Personio, a $3B+ HR and payroll platform with 1,500 employees, 15,000 customers, and a 400-person sales team. He shared their AI transformation journey at SaaStr AI London — and the learnings are a masterclass for any revenue leader trying to figure out how to actually deploy AI in GTM. We’re all hearing about AI-native companies crushing it. Replit, Gamma, Harvey. But w...
The Present and Future of AI in Sales and GTM A Deep Dive with Jason Lemkin and Kyle Norton, CRO at Owner 17.12.2025 1:59
Jason Lemkin led the seed round via SaaStr Fund in unicorn Owner.com , an AI solution revolutionizing how small restaurants manage their business. Kyle Norton joined shortly thereafter, and after a slow few months, Kyle rocketed the org to almost $100m ARR in just a few years -- with growth accelerating at scale. Both Kyle and Jason have shared AI agents, learnings, and more on their AI agent jour...
We Deployed 20+ AI Agents and Replaced Our Entire Human SDR Team. Here's What Actually Works. (Video + Pod) 12.12.2025 2:36
At SaaStr AI London , Amelia and I went deep on our AI SDR journey. We shared all our data, all the emails we’ve sent, all the performance metrics—everything. And the response was overwhelming. But here’s the thing: the #1 objection we kept hearing was “Yeah, but this won’t work for me . I don’t have your scale. I don’t have your data. I don’t have 10 years of history.” That’s simply not true. If...
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