SaaStr 838: The Present and Future of AI in Sales and GTM with SaaStr's CEO and Owner's CRO Jason Lemkin on Going All-In on AI Agents: 20 Agents, Zero SDRs, and the Death of Mid-Pack Sales Jason Lemkin, Founder and CEO of SaaStr, sits down with Kyle Norton, CRO at Owner, to share the raw story of how frustration with sales team turnover pushed him to deploy 20 AI agents in under a year, and why we'll never go back. In this episode, we cover: → Why Jason stopped hiring SDRs after two senior reps ...
Jan 21, 2026•56 min
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 th...
Jan 14, 2026•29 min
SaaStr 836: The Step-By-Step Playbook for Building AI-Powered GTM Teams with Personio's CRO Philip Lacor, CRO of Personio, shares his company's journey to building an AI-powered go-to-market motion, including 5 critical lessons learned and 4 real-world use cases delivering measurable results. In this podcast, Philip breaks down: ✅ The 5 lessons for AI transformation: top-down + bottom-up motion, cross-functional teams, prioritization frameworks, building AI culture, and combining great stack wit...
Jan 07, 2026•53 min
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 cop...
Jan 02, 2026•56 min
SaaStr 834: Why OpenAI Doesn't Pay Sales Commission (And Why It Works) with OpenAI GTM Leader Maggie Hott, and Harry Stebbings, Founder of 20VC Discover how OpenAI's unique approach to B2B sales compensation is changing the game. In this interview with Harry Stebbings, Founder of 20VC, Maggie Hott, OpenAI GTM leadership, shares her experience at OpenAI, including why they don't pay sales commissions, and what B2B sales leaders can learn from this disruptive model. --------------------- This epis...
Dec 24, 2025•36 min
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...
Dec 17, 2025•55 min
SaaStr 832: How to Use AI to Hyper-Customize Go-To-Market at Scale with SaaStr's CEO and Chief AI Officer In this episode from SaaStr AI London 2025, SaaStr CEO and Founder Jason Lemkin and SaaStr's Chief AI Officer, Amelia Lerutte discuss the implementation and optimization of AI SDRs within various business contexts. They focus on key AI agents used for sales processes, data aggregation, and the customization of outbound and inbound messages. Real-world results, like increased email response r...
Dec 10, 2025•48 min
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 p...
Nov 26, 2025•54 min
SaaStr 830: 6 Months Later, How Our AI SDRs Actually Work as AI Runs GTM with SaaStr's CEO and Chief AI Officer In this episode, SaaStr CEO and Founder Jason Lemkin and SaaStr's Chief AI Officer, Amelia Lerutte delve into their journey of integrating AI into our go-to-market strategy over the past six months. Starting with just one AI agent before SaaStr Annual in May, we've scaled to roughly 20 core agents by November, covering various use cases across marketing, sales, customer support, and op...
Nov 21, 2025•1 hr 25 min
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 pi...
Nov 12, 2025•26 min
SaaStr 828: The AI Revolution in B2B: Insights from SaaStr CEO Jason Lemkin and SaaStr Chief AI Officer Amelia Lerutte, and Qualified's CEO Kraig Swensrud Join Kraig Swensrud, founder and CEO of Qualified, as he sits down with Jason Lemkin, CEO & Founder SaaStr, and Amelia LeRutte, Chief AI Officer at SaaStr. In this insightful discussion, they explore the current landscape of AI in business, including the challenges and opportunities of integrating AI agents into companies. From the importa...
Nov 05, 2025•45 min
Brett Queener is Partner at Bonfire Ventures , a $1B AUM seed-stage fund writing $3-4M checks into application software companies. He was employee #70 at Salesforce.com, where he built go-to-market, launched the AppExchange, and helped scale the company from its earliest days. Previously, he worked at Siebel Systems (the fastest-growing software company of its era) and ran a B2B startup (SmartRecruiters) from pre-revenue to $100M ARR. He writes about the changing software industry in real-time a...
Oct 29, 2025•36 min
In this comprehensive session, SaaStr CEO and Founder Jason Lemkin dives into the latest trends and developments in AI, particularly in the go-to-market (GTM) sector. The session outlines how innovative AI tools are transforming businesses, from AI SDRs and BDRs to forward-deployed engineers. Leaders in the industry are pushing the boundaries, showing higher growth rates and superior marketing efficiency. We also discuss the importance of hands-on deployment and training of AI tools to achieve s...
Oct 22, 2025•49 min
SaaStr 825: How the AI Era Has Directly Impacted Marketing and Sales with Snowflake's CMO and Founding CRO Join us for an insightful episode discussing the impact of AI on marketing and sales at Snowflake. Hosts Chris Degnan, founding CRO of Snowflake, and Denise Persson, CMO at Snowflake, delve into how AI has revolutionized their operations. They share key learnings from Snowflake's data cloud market strategies and their record-breaking IPO. Discover the significance of company culture, securi...
Oct 15, 2025•40 min
SaaStr 824: VC in the AI Era - Exactly What's Getting Funded, Why & When with SaaStr CEO and Founder Jason Lemkin In this episode, SaaStr CEO and Founder Jason Lemkin delves into the current state of venture capital (VC) funding, informed by data from over a thousand reviewed pitch decks and approximately 400,000 startup valuations on SaaStr AI. Learn about the latest trends, what VCs are looking for, and what it takes to secure funding in today's market. We'll discuss the performance metric...
Oct 08, 2025•31 min
SaaStr 823: Is GTM Really Dead?! with SaaStr CEO Jason Lemkin In this episode, Jason Lemkin, SaaStr CEO and Founder, addresses common misconceptions about traditional go-to-market strategies in the age of AI. Despite claims that outbound marketing, SEO, and old-school tactics are dead, the speaker highlights how leading AI companies are successfully employing these methods with minor tweaks. Drawing from the success stories of OpenAI, Notion, Dialpad, and others, the presenter emphasizes the imp...
Oct 03, 2025•46 min
SaaStr 822: SaaStr's Top 10+ AI Agents: AI SDR, AI BDR, AI RevOps + More: The How, The Who, The Why with SaaStr CEO Jason Lemkin Join us in this comprehensive deep dive into the use of AI agents within SaaStr's operations, as requested by many of our followers. Led by SaaStr CEO and Founder, Jason Lemkin, and SaaStr Chief AI Officer, Amelia Lerutte, we'll detail our journey from having no AI at the start of the year to utilizing 20 different AI agents, including 11 core ones that we rely on dail...
Sep 24, 2025•54 min
SaaStr 821: Swapping Stories - Building AI-First Companies: Insights from Zapier's CEO and Co-Founder Wade Foster Join us for an in-depth conversation with Wade Foster, co-founder and CEO of Zapier, on the SaaStr AI Swapping Stories Podcast! Wade shares how Zapier is leading the way in AI-powered automation, the evolution from simple workflows to agentic systems, and why AI fluency is now a must-have for every new hire. In this episode, we discuss: The journey of Zapier from integration tool to ...
Sep 17, 2025•38 min
SaaStr 820: The Complete Guide to Vibe Coding Without a Developer with SaaStr CEO and Founder Jason Lemkin Join us in this episode as we dive into the world of vibe coding with a prosumer approach. SaaStr CEO and Founder Jason Lemkin shares his extensive journey of building production-ready applications without a developer, using platforms like Replit and Lovable. From initial excitement to hard-earned lessons, learn about the strengths, challenges, and key takeaways from creating and deploying ...
Sep 12, 2025•54 min
SaaStr 819: Swapping Notes on the AI Revolution in Marketing with G2's CMO Sydney Sloan Welcome to Swapping Notes, a new SaaStr podcast series where we cut through the AI hype and get real about who's doing what with AI in B2B. Amelia LeRutte, Chief AI Officer at SaaStr, and co-host Guillaume Cabane, Co-Founder and General Partner at HyperGrowth Partners, sit down with AI leaders from the companies to share notes and stories on what's working in AI. In this episode, we swap notes with G2's CMO, ...
Sep 10, 2025•32 min
SaaStr 818: Anthropic, Cursor, Fal & Bessemer: The Realities of Scaling AI Join Talia Goldberg (Bessemer Venture Partners), Kelly Loftus (Anthropic), Jacob Jackson (Cursor), and Gorkem Yurtseven (FaL - Feautres and Labels) as they discuss the evolving landscape of AI, business models, metrics, and the future of generative media. 00:00 - Introduction & Panelist Bios 01:19 - How AI Companies Are Changing Metrics 02:20 - The New Economics: Margins, Growth, and Pricing 04:41 - Usage-Based Mo...
Sep 05, 2025•31 min
div]:bg-bg-000/50 [&_pre>div]:border-0.5 [&_pre>div]:border-border-400 [&_.ignore-pre-bg>div]:bg-transparent [&_.standard-markdown_:is(p,blockquote,h1,h2,h3,h4,h5,h6)]:pl-2 [&_.standard-markdown_:is(p,blockquote,ul,ol,h1,h2,h3,h4,h5,h6)]:pr-8 [&_.progressive-markdown_:is(p,blockquote,h1,h2,h3,h4,h5,h6)]:pl-2 [&_.progressive-markdown_:is(p,blockquote,ul,ol,h1,h2,h3,h4,h5,h6)]:pr-8"> _*]:min-w-0 standard-markdown"> SaaStr 817: What Happens When AI Kills Y...
Aug 27, 2025•48 min
Join us as Jason Lemkin, CEO, and Founder of SaaStr, sits down with Tope Awotona, CEO, and founder of Calendly for an insightful AMA session. They discuss Calendly's journey, their success in the Product-Led Growth (PLG) domain, and how it balances self-serve with enterprise sales strategies. Tope shares candid lessons learned from growing Calendly, from managing customer acquisition costs to aligning product development with customer needs. The conversation also delves into how Calendly plans t...
Aug 20, 2025•32 min
SaaStr 815: Redpoint Ventures Playbook: How Top VCs Are Really Investing in AI with Jacob Effron, Managing Director of Redpoint Ventures Jacob Effron, Managing Director at RedPoint, discusses the state of AI investing and the rapid advancements in AI technology. He highlights the significant decrease in model costs, increased AI capabilities in applications like coding, voice models, and customer support, and the rapid scaling of AI startups. Jacob also talks about how venture capital strategies...
Aug 13, 2025•32 min
SaaStr 814: How to Build Top-Performing Sales Orgs with OpenAI's GTM Leader Maggie Hott Join Maggie Hott, GTM Leader at OpenAI, as she shares her extensive experience in building top-performing sales organizations at SaaStr. With a remarkable career history at Eventbrite, Slack, Webflow, and OpenAI, Maggie distills 15 years of insights into a tactical playbook for building and scaling sales teams. Learn key principles for hiring the right candidates, fostering thriving teams, maintaining custome...
Aug 06, 2025•42 min
In this session, CRO of ServiceTitan, Ross Biestman, and Chemistry's Managing Partner and Co-Founder, Kristina Shen, discuss ServiceTitan's founding principles and growth from a small company to a $11 billion vertical SaaS leader. Together they cover ServiceTitan's mission-driven approach, and its successful adoption of AI for operational efficiency. Ross shares personal anecdotes about customer interactions and pivotal moments leading to ServiceTitan's massive success. The episode underscores t...
Jul 30, 2025•33 min
SaaStr 812: What's Working Now: AI's Real Impact on Sales with SaaStr's CEO and Co-Founder, and SVP & GM Join Jason Lemkin, CEO and Founder of SaaStr, and Amelia Lerutte, SVP and GM of SaaStr as they dive deep into the practical applications, results, and learnings from integrating AI into sales workflows. This session covers the initial struggles, data preparation, and continuous optimization required to achieve high-quality outputs with AI. They share specific examples of what's working, t...
Jul 23, 2025•47 min
SaaStr 811: Marketing in the Age of AI with Wiz's CMO Raaz Herzberg Join us for an insightful discussion with Raaz Herzberg, the Chief Marketing Officer of Wiz, as she dives into her unconventional journey from engineering to leading Wiz's marketing strategy. In this episode, Raaz shares her unique perspectives on how a lack of traditional marketing background shaped her approach, focusing on building brand awareness and solving customer pain points. Learn about the innovative tactics she's empl...
Jul 16, 2025•41 min
SaaStr 810: AI and the Bottom Line, How Canva Turns Freemium into Conversions with Canva's CCO Rob Giglio Join John Gleason, founder and managing partner at Success Venture Partners, as he interviews Rob Giglio, Chief Customer Officer at Canva. Rob shares his extensive experience leading customer success, sales, and go-to-market functions at top companies like HubSpot, DocuSign, and Adobe. In this episode, Rob delves into his strategic approach to scaling Canva's enterprise business while mainta...
Jul 10, 2025•38 min
SaaStr 809: Why Enterprise AI Adoption Is Moving 5-10X Faster Than Cloud with Box's CEO and Co-Founder, IBM's VP for AI and SaaStr's CEO and Founder This conversation between Aaron Levie, CEO & Co-Founder of Box, Raj Datta, Global Vice President for Software and A.I. Partnerships at IBM and Jason Lemkin, CEO and Founder of SaaStr, covers the evolution from chat interfaces to digital labor models, the integration of AI to automate complex tasks, and the emergence of new paradigms for business...
Jul 02, 2025•38 min
