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

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 daily. Learn from our insights on our most utilized AI agents, their workings, actual data, and how we manage them for optimal results. Discover specific tools like Artisan, Qualified, Gamma, and Replit, and understand how they're integrated into our outbound, inbound, and sales processes. This episode also covers how we've internally developed AI-powered solutions for speaker application reviews, content review, startup valuation, and more. If you're interested in bringing intelligent automation to your business, this session offers practical advice and firsthand experiences to guide you on your AI journey. --------------------- This episode is brought to you by Intercom:   Fin is the #1 AI Agent for resolving complex queries like refunds, transaction disputes, and technical troubleshooting—all with speed and reliability. See how Fin can deliver the highest resolution rates and highest-quality customer experience at fin.ai/saastr.   --------------------- 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.

24 Sep 54min

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 AI orchestration platform Real-world examples of agentic workflows and automation at scale How Zapier’s culture embraces “don’t be a robot, build a robot” The impact of AI on sales, customer success, and internal operations Tips for companies looking to hire and upskill for an AI-first future The latest trends in AI tools, including voice-to-text and workflow automation Whether you’re a founder, operator, or just curious about the future of work, this episode is packed with actionable insights and inspiration. And see you at Zapconnect next week (sign up here - it's free.)  -----------------------------------------------------------------------    Fin is the #1 AI Agent for resolving complex queries like refunds, transaction disputes, and technical troubleshooting—all with speed and reliability. See how Fin can deliver the highest resolution rates and highest-quality customer experience at fin.ai/saastr.  --------------------- If you're serious about B2B and AI, you need to be in London this December 2nd and 3rd.   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.

17 Sep 37min

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 vibe-coded apps. Discover why the hype around 'building an app in 20 minutes' is often misleading, and understand the importance of thorough planning, competitive research, and mastering your platform. Whether you're a founder, aspiring app creator, or tech enthusiast, this episode will provide valuable insights into the future of no-code and low-code development.   ----------------------- This episode is sponsored by Intercom  Fin is the #1 AI Agent for resolving complex queries like refunds, transaction disputes, and technical troubleshooting—all with speed and reliability. See how Fin can deliver the highest resolution rates and highest-quality customer experience at fin.ai/saastr. --------------------- If you're serious about B2B and AI, you need to be in London this December 2nd and 3rd.   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 podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.

12 Sep 54min

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, Sydney Sloan. Together, we deep dive into the evolving role of AI in marketing and buyer behavior. We explore how AI is reshaping the buying process, the significance of brand trust, and the future of web experiences. The episode also covers the importance of AI orchestration roles and practical advice for founders and CMOs to adapt to the rapid advancements in AI tools and strategies. Tune in to discover insights on how to effectively integrate AI into your marketing efforts and stay ahead in the dynamic landscape. ---------------------   Fin is the #1 AI Agent for resolving complex queries like refunds, transaction disputes, and technical troubleshooting—all with speed and reliability. See how Fin can deliver the highest resolution rates and highest-quality customer experience at fin.ai/saastr. --------------------- If you're serious about B2B and AI, you need to be in London this December 2nd and 3rd.   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 podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.

10 Sep 31min

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 Models & The Cost to Serve 06:31 - The Impact of Expensive Models on Margins 08:00 - Go-To-Market Team Structures at Anthropic 09:36 - Scaling Sales Teams & The Quota Debate 12:01 - Hiring and Team Building Tactics 14:47 - How AI Is Used Internally at These Companies 17:47 - Key Decisions & Pivots in Company Journeys 20:07 - Collaboration vs. Competition: Cursor & Anthropic 22:23 - Measuring Productivity Gains from AI 24:26 - The Metrics That Matter Most 27:16 - Final Thoughts & Audience Q&A   --------------------- Fin is the #1 AI Agent for resolving complex queries like refunds, transaction disputes, and technical troubleshooting—all with speed and reliability. See how Fin can deliver the highest resolution rates and highest-quality customer experience at fin.ai/saastr. --------------------- If you're serious about B2B and AI, you need to be in London this December 2nd and 3rd.   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 podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.

5 Sep 30min

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 Your SaaS Growth? Live Q&A with SaaStr CEO and Founder Jason Lemkin In this Q&A session from SaaStr Annual, Jason Lemkin delivers hard truths about how AI is reshaping the entire SaaS landscape. No sugarcoating, no feel-good platitudes - just the brutal reality of what's happening to B2B companies right now. What You'll Learn: Why 80% of B2B investors now only do AI deals (and what that means for traditional SaaS) The real reason $100M revenue companies are suddenly hitting growth walls Why VCs have shifted from seeking billion-dollar to trillion-dollar outcomes How the "triple-triple-double-double" growth model died in 18 months Why you need to go multi-product by $10M revenue (not $100M) The downward death spiral killing SaaS companies that aren't adapting Specific tactics for surviving when your go-to-market playbook stops working Key Moments: A founder admits he's "terrified" of AI - Jason's response will surprise you Why vertical SaaS is becoming the only "safe haven" The harsh math on fundraising when you're not AI-first How brand marketing is changing as search moves from Google to ChatGPT Why working "twice as hard and four times smarter" isn't optional anymore Raw Founder Questions Answered: "How do I fundraise when I'm not AI-first?" "Is triple-double-double still attractive to investors?" "Should my sales team experiment with AI?" "How many resources should we devote to becoming AI-first?" This isn't your typical conference recap. It's 90 minutes of unvarnished insights from founders in the trenches, dealing with the AI disruption in real-time. Jason doesn't hold back on what's working, what's broken, and what you need to do differently starting tomorrow. Perfect for: SaaS founders, revenue leaders, and anyone trying to navigate the AI transformation of B2B software. ------------------   Hey everybody, SaaStr AI's next stop takes us to London on December 2nd and 3rd!   It's Christmas with SaaStr and 2,000 of the best SaaS and AI leaders.    The biggest names will be there. The best networking.    Early adopter tickets are selling faster than we expected. So don't wait. With only 5 months until the event, we expect this year's SaaStr London event to sell out to capacity.    Use my code jason20pod for exclusive savings. Get your tickets now at podcast.saastrlondon.com or use code jason20pod at checkout.   SaaStr AI London – where SaaS Meets AI in London. See you there. --------------------------------------------------- Hey everybody, SaaStr Annual will be back in May of 2026.  The world's largest SaaS + AI gathering for executives. Just this May we hosted: 10,000 attendees with 68% VP-level and above, 36% CEOs and founders and a growing 25% were 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. Use my code JASON100 for exclusive savings. Get your tickets at podcast.saastrannual.com or use code JASON100 at checkout.  SaaStr Annual 2026. We'll see you there.

27 Aug 48min

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 to integrate AI to enhance user productivity and manage meetings more efficiently. This episode is packed with valuable insights for founders, CEOs, and anyone interested in SaaS growth strategies. ------------------   Hey everybody, SaaStr Annual will be back in May of 2026.  The world's largest SaaS + AI gathering for executives. Just this May we hosted: 10,000 attendees with 68% VP-level and above, 36% CEOs and founders and a growing 25% were 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. Use my code JASON100 for exclusive savings. Get your tickets at podcast.saastrannual.com or use code JASON100 at checkout.  SaaStr Annual 2026. We'll see you there

20 Aug 31min

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 have shifted, with a focus on AI-driven end-use cases and quality. He outlines a three-part investment framework focused on identifying effective AI applications and the potential for future expansion. Effron shares insights on successful AI companies like Abridge and Lara, emphasizing their high-quality products and rapid market adaptation. He concludes by noting the importance of brand building, velocity in product development, and the evolving landscape of AI investments. 00:00 Introduction and Speaker Background 00:25 Current Trends in AI and Model Costs 01:30 Implications for AI Application Companies 05:06 Challenges in the AI Investment Landscape 09:07 Effective AI Application Companies 10:59 Investment Framework for AI Companies 15:14 Case Studies: Abridge and Lara 21:38 Key Learnings and Final Thoughts 23:38 Q&A Session

13 Aug 31min