The Official SaaStr Podcast: SaaS | Founders | Investors

• SaaStr 816: PLG to Enterprise to SMB: Insights from Calendly's CEO

  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

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• SaaStr 815: Redpoint Ventures Playbook: How Top VCs Are Really Investing in AI

  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    

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• SaaStr 814: How to Build Top-Performing Sales Orgs with OpenAI's GTM Leader Maggie Hott

  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 customer obsession, and driving sustainable growth. Discover common pitfalls to avoid, the importance of storytelling, and how to align your teams for maximum impact. Whether you're a startup founder or a seasoned leader, these practical lessons will help you scale your sales team effectively.     ------------------ 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.   ------------------ This episode of the SaaStr podcast is sponsored by: get.tech The best .coms are taken or overpriced. So you settle on a workaround domain for your website. Don't compromise. Get a clean, sharp .tech domain that instantly says: this is a tech startup. Grab yours at get.tech/saastr or via domain registrars like GoDaddy.

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• SaaStr 813: From Startup to $11B: ServiceTitan's CRO Breaks Down Their Sales Playbook

  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 the importance of on-site customer interactions and the role of AI and disciplined expansion in their growth strategy. ------------------ This episode of the SaaStr podcast is sponsored by: get.tech The best .coms are taken or overpriced. So you settle on a workaround domain for your website. Don't compromise. Get a clean, sharp .tech domain that instantly says: this is a tech startup. Grab yours at get.tech/saastr or via domain registrars like GoDaddy. ------------------ 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. 

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• SaaStr 812: What’s Working Now: AI’s Real Impact on Sales with SaaStr's CEO and Co-Founder, and SVP & GM

  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, the importance of human oversight, and the benefits of combining AI with human expertise. Whether you're initiating outbound sales or reactivating lapsed accounts, learn how SaaStr successfully increased response rates and closed deals using AI-driven strategies. ------------------ This episode of the SaaStr podcast is sponsored by: get.tech The best .coms are taken or overpriced. So you settle on a workaround domain for your website. Don't compromise. Get a clean, sharp .tech domain that instantly says: this is a tech startup. Grab yours at get.tech/saastr or via domain registrars like GoDaddy. ------------------   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

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