Jason Lemkin

Julian Lehr asked a good question the other day on X: what if Slack had never sold to Salesforce, stayed in founder mode, and went hard at AI? What would the product look like, and what would it be trading at? What would an independent Slack look like today? Probably $2.5B ARR growing 25%, trading... Continue Reading

We run 21 AI agents in production at SaaStr. They have closed millions in revenue. They book meetings on Saturday nights, resurrect leads nobody had touched in six months, run the invoice and the collections follow-up, and write to Salesforce all day without asking anyone for permission. It’s so great and so disruptive, and now... Continue Reading

CRO Confidential: 0 to $600M in Under 4 Years. The ElevenLabs GTM Playbook with Carles Reina (Partner @ Baobab Ventures and Former VP of Revenue at ElevenLabs). Hosted by Sam Blond, CEO and Co-Founder of Monaco Carles Reina was the fourth employee and first GTM hire at ElevenLabs. Four years later, the company hit $600M ARR and an $11B valuation. In this episode of CRO Confidential, Carles breaks down exactly how they built it. He covers the distribution-first strategy that drove 0 to $100M in 20 months, the grants program that pulled demand away from every competitor in the market, and the 20X quota model that had reps hitting 300-600% attainment. He also gets into what he'd do differently — why sales enablement and senior sellers should come earlier than most founders think — and how ElevenLabs wired AI into their GTM motion before most companies were even asking the question. If you're building go-to-market from scratch or trying to figure out what "AI-native" revenue looks like in practice, this one is required listening. ----------------------------------------------------------- Want to join the SaaStr community? We're the 🌎largest community for B2B software. Subscribe for weekly updates: https://www.saastr.com/subscribeform Twitter: https://twitter.com/saastr LinkedIn: https://www.linkedin.com/company/2724976 Quora Group: https://www.quora.com/q/cloud Facebook: https://www.facebook.com/SaaStr/ Instagram: https://www.instagram.com/saastr/ Our North American Event: https://bit.ly/2OXeAYh Our European Event: https://bit.ly/2OZTad8

Building AI agents is one thing. Shipping them to enterprise customers who will hold you responsible for every mistake they make is something else entirely. Jason Lemkin sits down with the CPOs of three of the most ambitious enterprise AI companies - Rubrik, Glean, and Harvey - for an unfiltered conversation on what it actually takes to go agentic in production. Not demos, not roadmaps, actual working agents at scale, inside security, legal, and enterprise search. Rubrik's CPO breaks down how they're building Ruby, their agentic interface for cyber recovery - and why determinism matters when your agent is making decisions about someone's core infrastructure. When an agent makes a mistake at Rubrik, the blast radius isn't a bad email. It's a broken recovery workflow. Emrecan Dogan (Glean) shares how Glean has evolved from enterprise search to a full system of intelligence - powering agents that run on behalf of entire departments, not just individual users. Plus: why MCP alone isn't enough, and what offline-processed context gives you that runtime fetch never will. Anique Drumright (Harvey) explains how Harvey deploys legal engineers - ex-lawyers with 8 to 10 years of practice - with every enterprise customer, and why that human expertise in the deployment pod is what makes agentic workflows actually stick in law firms. The group also digs into the question nobody wants to answer: when your agent takes an action and something goes wrong, who's responsible? And what does it mean to build a product when customers are going to use it in ways you never anticipated? If you're building agents, buying agents, or trying to figure out how to monetize AI in a market that's moving faster than any product roadmap can keep up with, this one is worth your time. Timestamps: 00:00 - Intro: from the cushiest to the most stressful job in B2B 04:00 - Rubrik: building agents for cyber recovery without breaking production 12:00 - Glean: from search to system of intelligence 20:00 - Harvey: why the whole platform is agentic and what that means 28:00 - Live demos: Rubrik's Ruby, Glean's revenue ops agent 40:00 - Who's responsible when agents fail? 48:00 - Forward deployed legal engineers and the Harvey deployment model 55:00 - Q&A SaaStr hosts the world's largest community for B2B software founders and executives.

Who Owns Your Data Now? Agents vs. System of Record, ServiceTitan vs. Podium, Headless Salesforce, and Agentic Renewals on The Agents #013 The agents are writing data faster than any human ever could - and systems of record aren't ready for it. This week on The Agents, Jason and Amelia dig into the biggest meta-theme of 2026: what happens when your AI agents become the primary user of your CRM, your MAP, and every other system you've built your business on? Together, they unpack the ServiceTitan vs. Podium blowup, where an agentic lead gen tool slowly became a competing system of record until ServiceTitan shut them off with 30 days' notice, and why this is just the first of many fights like it coming across SaaS. Then Amelia pulls back the curtain on how SaaStr actually runs Salesforce headless through 10K, what it means that their agents have written 40 gigabytes of data into Salesforce without either of them logging in, and why the storage math is going to force a reckoning for every vendor jacking up API prices right now. Plus: the renewal agent Amelia built that generates a fully custom, hyper-personalized pitch deck for every single customer, using headless Salesforce, Gamma, social data, podcast mentions, and Gmail. And why Clay plus ZoomInfo plus Cowork turned out to be the best enrichment stack their agents have found yet. If you're building on top of systems of record, selling to companies that are, or just trying to figure out how agents change the economics of SaaS data, this one is essential listening. Timestamps: 00:00 - Intro 02:00 - ServiceTitan cuts off Podium: what happened and why it matters 10:00 - 40 gigs in Salesforce and neither of us logged in 16:00 - The API pricing reckoning coming for systems of record 22:00 - How SaaStr runs Salesforce headless with 10K 30:00 - The renewal agent: no account left behind 42:00 - Narrative-first pitching: getting the agent to sell 50:00 - Clay + ZoomInfo + Cowork: the enrichment stack that actually worked 58:00 - What comes next: agentic inbound proposals SaaStr hosts the world's largest community for B2B software founders and executives. -------------------------------------------------- Want to join the SaaStr community? We're the 🌎largest community for B2B software. Subscribe for weekly updates: https://www.saastr.com/subscribeform Twitter: https://twitter.com/saastr LinkedIn: https://www.linkedin.com/company/2724976 Quora Group: https://www.quora.com/q/cloud Facebook: https://www.facebook.com/SaaStr/ Instagram: https://www.instagram.com/saastr/ Our North American Event: https://bit.ly/2OXeAYh Our European Event: https://bit.ly/2OZTad8

AI agents aren't just tools; they're relentless testers, repeating tasks thousands of times. Building software? Expect agents to be your super users, demanding robust experimentation. #AIAgents #SoftwareDevelopment #FutureTech #MachineLearning

Learn how AI is transforming roles at Klaviyo. Employees with AI skills can take on bigger projects and achieve massive success in the coming years. Explore system decomposition and the future of work. #AISkills #FutureOfWork #Klaviyo #TechInnovation #CareerDevelopment

Great VP of Sales, first week: – brings 2-4 great sales execs in ASAP. often week 1– identifies top existing talent, does what it takes to keep them– begins to move out underperformers– jumps into all critical deals Mediocre VP of Sales, first month: – has no one to bring… — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk)... Continue Reading

"The #1 mistake founders make when they hire their first VP of Sales? Or even just their first sales rep? They step back from sales. No. You don't get that time back. It's just what you do in sales, changes." pic.twitter.com/wwUzRvrbt0 — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) July 29, 2026 Dear SaaStr: When Should The CEO... Continue Reading

"How do you kill your competition? You have to think about this if you really want to win. At Elevenlabs, we did a grants program, 10,000+. Then we upsold them — later. And it helped crush the competition." with @samdblond https://t.co/ktEXlxMQJV pic.twitter.com/CglTU9LMqm — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) September 13, 2026 IMHO and experience, most B2B... Continue Reading