The Official SaaStr Podcast: SaaS | Founders | Investors

SaaStr 853: The Agents #004: Tragedy Apps, Too Many AI SDRs, and Why Your Next Hire Should Report to an Agent Your AI SDR pitches are getting better, but your AI PR pitches are getting you blocked. Jason and Amelia break down why the gap between good and great agents is the difference between pipeline and the spam folder. Then they introduce "tragedy apps," the term for products that had every advantage in the AI era and blew it. Descript had the customers, the product, and the timing, and froze. Replit waited 10 years for its moment and seized it. The lesson: catching up isn't enough if you're not building something new. Plus, the SaaStr team built an AI API Report Card that grades every major SaaS API on how agent-friendly it is (Stripe got the only A+, Marketo got a C, and no, they're not surprised). Jason and Amelia also get honest about running 4-5 AI SDRs from different vendors, why they'll probably have 6 by year end, and why single-vendor consolidation isn't the answer yet. And the wildest part: their AI VP of Marketing, 10K, now generates 3 actionable campaign ideas a day, runs autonomous campaigns on weekends, and might be a better boss than either of them. They're seriously hiring a human marketer whose primary manager would be the agent. Not a joke. Not a thought experiment. A real job posting. Finally, if your team is resisting AI, stop worrying about change management. Just hire one senior person who's all-in on agents and let the rest sort itself out.

SaaStr 841: Going From Blobs to Billions. Clay's Co-Founder Breaks Down Inbound, Outbound, and AI-Powered Sales. Clay's Co-Founder Varun Anand takes the stage at SaaStr to break down how the company went from paying for claymation blobs before generating any revenue to powering growth workflows for companies like Cursor, Anthropic, and Figma. He explains why brand has always been core to Clay's identity, how their CFO roast videos and creative campaigns are actually capturing mindshare in a world where B2B marketing is painfully boring, and why he pushes back on the "use AI for everything" mentality that's taken over the industry. Varun does a full live demo building an inbound qualification workflow from scratch using real audience volunteers, walking through everything from lead enrichment and waterfall data sourcing to AI-powered scoring, personalized meme generation, research brief creation, and CRM updates. He also brings audience members on stage to do live growth hacking for their actual business problems. Beyond the product, this session goes deep on hiring. Varun shares the origin story of the GTM Engineer role, how it went from an internal job title for Clay's non-traditional sales team to the most in-demand position in B2B SaaS, and what he actually looks for when evaluating candidates (hint: it's creativity, not a traditional sales background). He talks about Clay's take-home process, work trials, why they hire generalists who commit to specific roles, and the surprising backgrounds of some of their best hires. Whether you're building out your go-to-market motion, thinking about how to use AI without losing what makes your brand unique, or just trying to figure out what a GTM Engineer actually does, this session covers it all. --------------------- This episode is Sponsored in part by HappyFox: Imagine having AI agents for every support task — one that triages tickets, another that catches duplicates, one that spots churn risks. That'd be pretty amazing, right? HappyFox just made it real with Autopilot. These pre-built AI agents deploy in about 60 seconds and run for as low as 2 cents per successful action. All of it sits inside the HappyFox omnichannel, AI-first support stack — Chatbot, Copilot, and Autopilot working as one. Check them out at happyfox.com/saastr --------------------- Hey everybody, the biggest B2B + AI event of the year will be back - SaaStr AI in the SF Bay Area, aka the SaaStr Annual, will be back in May 2026. With 68% VP-level and above, 36% CEOs and founders and a growing 25% AI-first professional, this is the very best of the best S-tier attendees and decision makers that come to SaaStr each year. But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait. Lock in your spot today by going to podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.

SaaStr 839: Why Most SaaS Companies Will Fail at AI (And How to Avoid It) with Intercom's CPO The Brutal Truth About Transforming a SaaS Company into an AI Company Intercom's Chief Product Officer, Paul Adams, shares the unfiltered story of how they transformed from a struggling SaaS company with 5 quarters of declining growth into an AI-first company with a breakthrough product (Fin) that now handles 1M+ customer resolutions per week. What You'll Learn: Why AI transformation requires "refounding" your entire company - not just adding AI features The self-harming decisions you must make to win (including parting ways with ~33% of your team) How to go from 0 to 6,000+ AI customers with 65% average resolution rate Why demos ≠ products and the "marketing overhang" problem The complete shift in how you build software (empirical evaluation vs. traditional product development) Why designers now ship code to production at Intercom How the buyer has changed (hint: it's no longer just the department head) --------------------- This episode is Sponsored in part by HappyFox: Imagine having AI agents for every support task — one that triages tickets, another that catches duplicates, one that spots churn risks. That'd be pretty amazing, right? HappyFox just made it real with Autopilot. These pre-built AI agents deploy in about 60 seconds and run for as low as 2 cents per successful action. All of it sits inside the HappyFox omnichannel, AI-first support stack — Chatbot, Copilot, and Autopilot working as one. Check them out at happyfox.com/saastr --------------------- Hey everybody, the biggest B2B + AI event of the year will be back - SaaStr AI in the SF Bay Area, aka the SaaStr Annual, will be back in May 2026. With 68% VP-level and above, 36% CEOs and founders and a growing 25% AI-first professional, this is the very best of the best S-tier attendees and decision makers that come to SaaStr each year. But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait. Lock in your spot today by going to podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.

SaaStr 837: 10 Things To Do Right Now to Become AI Native with Filevine's CEO & Founder Ryan Anderson, Co-Founder and CEO of Filevine, shares the playbook for how his legal tech company successfully transitioned from a traditional SaaS business to an AI-native company, now generating more new revenue from AI products than their core SaaS platform. With 6,000 customers, 700 employees, and $200M+ ARR growing at nearly 60%, Filevine has cracked the code on AI transformation. Ryan breaks down the strategic, technical, and cultural changes required to make the shift. Key Takeaways: Nothing is Sacred – Be prepared to tear down working systems that don't serve your AI future. Use a simple framework: keep what's critical to your competitive moat and keeps you fast; eliminate what slows you down. Content → Context – Your SaaS data becomes the competitive advantage when it serves as context for AI agents. Think Cher's closet in Clueless—you need both the organized system AND the AI. Restructure Your Architecture – AI can't just be "sprinkled on top." Your ML team needs to own the AI data layer and iterate daily without bottlenecks. Hire AI Natives – They want access to rich data and distribution. Sell them on what you have that AI-only startups don't. Consider Acquisitions – Filevine acquired Parrot to jumpstart their ML capabilities. Speed matters. Rebrand with Intent – Signal the change internally and externally. It's symbolic but powerful. Obsess Over Usage – If you can't measure it, don't ship it. Track DAU/WAU/MAU religiously. Leverage Your Data – Control API access, monitor AI traffic for product ideas, and don't give away your advantage for free. Price to Dominate – Your high SaaS margins let you undercut AI-only competitors on blended gross margin. Build One Product – Stop selling to customers who won't buy AI. Assume AI is implicit in everything you build. About the Speaker: Ryan Anderson is the Co-Founder and CEO of Filevine, an AI-powered legal operating system. Under his leadership, Filevine has achieved 96% gross revenue retention and 124% net revenue retention while successfully pivoting to AI-native operations. --------------------- This episode is Sponsored in part by HappyFox: Imagine having AI agents for every support task — one that triages tickets, another that catches duplicates, one that spots churn risks. That'd be pretty amazing, right? HappyFox just made it real with Autopilot. These pre-built AI agents deploy in about 60 seconds and run for as low as 2 cents per successful action. All of it sits inside the HappyFox omnichannel, AI-first support stack — Chatbot, Copilot, and Autopilot working as one. Check them out at happyfox.com/saastr --------------------- Hey everybody, the biggest B2B + AI event of the year will be back - SaaStr AI in the SF Bay Area, aka the SaaStr Annual, will be back in May 2026. With 68% VP-level and above, 36% CEOs and founders and a growing 25% AI-first professional, this is the very best of the best S-tier attendees and decision makers that come to SaaStr each year. But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait. Lock in your spot today by going to podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.

SaaStr 835: AI + B2B in 2026: Find the Tailwinds or Get Left Behind with SaaStr CEO and Founder Jason Lemkin Software spend is set to hit record levels in 2026, but you're not getting any of it unless you change. SaaStr CEO and Founder Jason Lemkin breaks down the paradox facing B2B companies right now: It's never been easier to scale to $100M (for a select few), while everyone else struggles. Half of all VC dollars are going into just 4 deals. IPOs ended the year with a whimper. And that AI copilot you built? It doesn't count. In this session, Jason shares the data on what's actually happening and what you need to do to capture your share of the hundreds of billions flowing into software. Key insights: Why "seed is for suckers" in today's VC environment The 3 types of AI products that unlock budget (and the one that doesn't) Why 30% of new IT budget is going to AI and how to steal it The TAM expansion math behind Cursor, Gamma, and AI SDR tools Why copilots and AI features alone won't save you The efficiency metrics every founder needs to track in 2026 If you didn't reaccelerate growth in 2025, you get a D. You can't get a D in 2026. 🎤 Recorded at SaaStr London AI Summit | December 2025 --------------------- This episode is Sponsored in part by HappyFox: Imagine having AI agents for every support task — one that triages tickets, another that catches duplicates, one that spots churn risks. That'd be pretty amazing, right? HappyFox just made it real with Autopilot. These pre-built AI agents deploy in about 60 seconds and run for as low as 2 cents per successful action. All of it sits inside the HappyFox omnichannel, AI-first support stack — Chatbot, Copilot, and Autopilot working as one. Check them out at happyfox.com/saastr --------------------- Hey everybody, the biggest B2B + AI event of the year will be back - SaaStr AI in the SF Bay Area, aka the SaaStr Annual, will be back in May 2026. With 68% VP-level and above, 36% CEOs and founders and a growing 25% AI-first professional, this is the very best of the best S-tier attendees and decision makers that come to SaaStr each year. But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait. Lock in your spot today by going to podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.

SaaStr 833: AI and the Death of the 2021 Sales Playbook with SaaStr CEO and Founder Jason Lemkin Join SaaStr CEO and Founder Jason Lemkin from SaaStr London as we tackle pressing topics in AI and sales during an engaging AMA session. From discussing the evolution of inbound vs. outbound sales to detailing the transformative impact of AI on sales roles and outbound strategies, this session covers it all. Learn about the importance of product expertise for selling AI solutions, the rise of AI SDRs, and why knowing your top three problems is crucial for effective outbound marketing. Plus, discover insights on the rapidly improving capabilities of AI agents and their implications for competitive moats. Whether you're a sales professional, marketer, or tech enthusiast, this episode is packed with actionable insights and future trends in the AI landscape. --------------------- This episode is Sponsored in part by HappyFox: Imagine having AI agents for every support task — one that triages tickets, another that catches duplicates, one that spots churn risks. That'd be pretty amazing, right? HappyFox just made it real with Autopilot. These pre-built AI agents deploy in about 60 seconds and run for as low as 2 cents per successful action. All of it sits inside the HappyFox omnichannel, AI-first support stack — Chatbot, Copilot, and Autopilot working as one. Check them out at happyfox.com/saastr --------------------- Hey everybody, the biggest B2B + AI event of the year will be back - SaaStr AI in the SF Bay Area, aka the SaaStr Annual, will be back in May 2026. With 68% VP-level and above, 36% CEOs and founders and a growing 25% AI-first professionals, this is the very best of the best S-tier attendees and decision makers that come to SaaStr each year. But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait. Lock in your spot today by going to podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.

SaaStr 831: How We Use 20+ AI Agents for Marketing & Go-to-Market with SaaStr's Chief AI Officer and CEO & Founder Join us for part two of our series on leveraging AI tools for Go-To-Market in B2B/SaaS. In this episode, SaaStr's CEO and Founder Jason Lemkin, and SaaStr's Chief AI Officer, Amelia Lerutte discuss the importance and current state of AI in marketing, highlighting their key tech stack and tools. They share their experiences and insights in utilizing these tools for creating personalized marketing collateral, automating content repurposing, and optimizing email campaigns with AI. Learn about the convergence of sales and marketing tools, the future of AI in go-to-market strategies, and how specialized AI agents can dramatically improve your outreach, lead generation, and content creation processes. --------------------- This episode is Sponsored in part by Salesforce: Connect data, automate busywork and empower teams like nobody's business with the one platform that grows with you, every step of the way. Learn how Salesforce works for Startups at salesforce.com/smb. --------------------- This episode is Sponsored in part by HappyFox: Imagine having AI agents for every support task — one that triages tickets, another that catches duplicates, one that spots churn risks. That'd be pretty amazing, right? HappyFox just made it real with Autopilot. These pre-built AI agents deploy in about 60 seconds and run for as low as 2 cents per successful action. All of it sits inside the HappyFox omnichannel, AI-first support stack — Chatbot, Copilot, and Autopilot working as one. Check them out at happyfox.com/saastr --------------------- Hey everybody, the biggest B2B + AI event of the year will be back - SaaStr AI in the SF Bay Area, aka the SaaStr Annual, will be back in May 2026. With 68% VP-level and above, 36% CEOs and founders and a growing 25% AI-first professional, this is the very best of the best S-tier attendees and decision makers that come to SaaStr each year. But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait. Lock in your spot today by going to podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.

SaaStr 829: A Hands-On Guide to SaaStr's New AI Tools with SaaStr CEO and Founder Jason Lemkin We delve into the functionalities of our SaaStr AI tools, including the AI Mentor, which has been engaged over 100,000 times, providing answers to various startup-related queries. You'll see a demonstration of how our AI VC tools, including a startup valuation calculator, pitch deck analyzer, and benchmarking tool, work effectively to help startups understand their valuations, get honest feedback on pitch decks, and connect with VCs. Additionally, explore our newly launched VC matchmaking system and other AI agents that have been integral in automating and enhancing SaaStr's operations. Experience these tools firsthand and discover how they can add value to your startup journey. Visit SaaStr.ai to access these tools for free and see the comprehensive suite of AI agents that we use. 00:00 Introduction and Overview 00:14 Exploring SaaStr AI Tools 01:15 Deep Dive into Digital Jason 04:20 AI VC Tools and Fundraising 05:26 Startup Valuation Calculator 06:07 Pitch Deck Analyzer 16:16 Benchmarking Your Startup 18:51 VC Matchmaking and Research 21:58 Conclusion and Q&A --------------------- This episode is Sponsored in part by Salesforce: Connect data, automate busywork and empower teams like nobody's business with the one platform that grows with you, every step of the way. Learn how Salesforce works for Startups at salesforce.com/smb. --------------------- If you're serious about B2B and AI, you need to be in London this December. SaaStr AI London is bringing together more than 2,000 leaders and founders for two days of practical advice on scaling into the new year. We'll have speakers flying in from OpenAI, Wiz, Clay, Intercom, and all your favorite SaaS companies, including yours truly with Harry Stebbings for a live 20VC podcast. It'll be fun, and it's all in the heart of London. Don't miss out: get your tickets with my exclusive discount by going to podcast.saastrlondon.com --------------------- Hey everybody, the biggest B2B + AI event of the year will be back - SaaStr AI in the SF Bay Area, aka the SaaStr Annual, will be back in May 2026. With 68% VP-level and above, 36% CEOs and founders and a growing 25% AI-first professional, this is the very best of the best S-tier attendees and decision makers that come to SaaStr each year. But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait. Lock in your spot today by going to podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.