The Official SaaStr Podcast: SaaS | Founders | Investors

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 onl...

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 alig...

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...

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....

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 i...

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 re...

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 buil...

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...

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,...

SaaStr 808: AI and Cybersecurity: Scaling Rubrik to a Billion Dollar Enterprise with Rubrik's Co-Founder and CTO In this episode, Kit Colbert, former CTO of VMware and Platform CTO at Invisible, sits down with Arvind  Nithrakashyap, Co-founder and CTO of Rubrik, to discuss the company's journey and innovations over the last 11 years.    Arvind  shares insights into Rubrik's platform for cyber resi...

SaaStr 807: Snowflake's CEO on the AI Data Cloud, Partner Strategy, and What's Next Join Sridhar Ramaswamy, CEO of Snowflake, and Jeremy Burton, CEO of Observe, in a comprehensive discussion led by SaaStr CEO & Founder, Jason Lemkin. Discover the inner workings of Snowflake's Board, the dynamics of strategic partnerships, and the evolving role of AI in data management. Learn how Snowflake aims to...

SaaStr 806: How The Smartest Founders Are Already Winning with AI: SaaStr CEO Jason Lemkin on My First Million   SaaStr CEO and Founder Jason Lemkin recently returned to HubSpot's My First Million Podcast with Sam Parr and Shaan Puri to do a deep dive on AI and SaaS. It was a fun one because we approached it more from a content creator and end-user perspective than from a software builder perspect...

SaaStr 805: CRO Confidential - 5 Ways AI Has Already Changed SaaS Sales Forever with Perplexity's CBO Dmitry Shevelenko. Hosted by Sam Blond. Join Sam Blond in the latest episode of CRO Confidential live from SaaStr Annual, featuring Dmitry Shevelenko, Chief Business Officer at Perplexity. Dive deep into how cutting-edge AI can transform your go-to-market strategies, sales processes, and organizat...

SaaStr 804: AI and The Future of Sales, Marketing & CS with HubSpot CEO Yamini Rangan Join us as HubSpot's CEO Yamini Rangan delves into the dynamic landscape of SaaS, discussing the rapid transformations driven by AI. In this insightful session, Yamini shares her experience with pivoting HubSpot's roadmap after the advent of ChatGPT, the increasing role of AI in product development, and the evolv...

SaaStr 803: AI, Sales + GTM in 2025/2026: This Really Changes Everything with SaaStr CEO and Founder Jason Lemkin and Owner CRO Kyle Norton In this engaging session, we dive deep into how AI is transforming the sales landscape, featuring a conversation between SaaStr CEO and Founder Jason Lemkin and Kyle Norton, the Chief Revenue Officer of Owner, a company recently valued at over a billion dollar...

SaaStr 802: SaaS + AI: It's Time to Move Much Faster with SaaStr CEO and Founder Jason Lemkin Join SaaStr CEO and Founder Jason Lemkin in this compelling podcast that was recorded live from SaaStr Annual, as he discusses the rapid transformation in the SaaS industry driven by AI advancements. Reflecting on changes since last September, Jason emphasizes the necessity for SaaS leaders and companies...

SaaStr 801: AI, M&A, and the Future of SaaS: Lessons from Marc Benioff, Chair, CEO & Co-Founder of Salesforce Join us for as SaaStr CEO and Founder Jason Lemkin sits down for a conversation with Mark Benioff, the CEO, Chair and Co-Founder of Salesforce. Together, we delve into the practical applications of AI in the B2B space. With 40 billion under Salesforce's belt, this discussion sheds light on...

SaaStr 800: 10 Ways AI Is Going to Change Sales. For Real with SaaStr CEO and Founder Jason Lemkin

SaaStr 799: The Series A Landscape in 2025: Insights from Chemistry VC's Ethan Kurzweil SaaStr CEO and Founder Jason Lemkin and Ethan Kurzwiel, previously partner at Bessemer Venture Partners and now founding partner at Chemistry VC, took us through a deep dive of exactly where Series A funding is right now in 2025. Current State of Early-Stage Venture Market The early-stage venture landscape has...

SaaStr 798: The Top 10 Reasons to Come to 2025 SaaStr Annual May 13-15 in SF Bay with SaaStr CEO Jason Lemkin SaaStr Annual is almost here! And we delve into the key reasons why you should attend SaaStr Annual 2025, happening from May 13th to 15th in the SF Bay Area. Learn about the unparalleled networking opportunities, including opt-in one-on-one meetings, braindates, and C-level summits. Discov...

Join Jason Lemkin and Sam Blond as they discuss the evolving role of AI in sales and marketing. Featuring insights from SaaStr's CRO Confidential Series with Rippling, Databricks, and Toast, this episode explores how AI is reshaping the sales landscape. Learn about the impact of AI on productivity, the effectiveness of cold calls, and how technical sales require specific expertise. Don't miss out...

SaaStr 796: The Secrets Inside Google Cloud's Growth with Sarah Kennedy, Vice President Google Cloud Marketing   In our latest episode of the SaaStr What's New series, SaaStr CEO and founder Jason Lemkin spoke with Sarah Kennedy, VP of Google Cloud Marketing. The conversation explores the explosive growth of Google Cloud and what's driving this momentum. Kennedy highlights the critical role AI pla...

SaaStr 795: The AI Impact on Banking and Finance with CEO and Co-founder at Treasury Prime, Chris Dean Join SaaStr CEO and Founder Jason Lemkin and Chris Dean from Treasury Prime as they delve into the intricate world of Banking as a Service (BaaS) and FinTech. The discussion spans a host of critical topics, including the fallout from Silicon Valley Bank, the complexities of reconciliation, Synaps...

SaaStr 794: The Top 10 Customer Success Metrics Investors Care About in 2025 with Gainsight CEO Nick Mehta   Nick Mehta is the CEO of Gainsight, the customer success platform that helps businesses deliver value to customers and drive scalable growth.   Over the past 12 years, Nick has met with more than 5,000 companies and hundreds of investors, becoming one of the foremost authorities on customer...

SaaStr 793: The 10-Point Checklist For When You Sell Your Company with David Frankel Managing Partner at Founder Collective and SaaStr CEO and Founder Jason Lemkin David Frankel is Managing Partner at Founder Collective, a successful seed fund with investments in companies like The Trade Desk, Olo, and Coupang. With decades of experience as both a founder and investor, David brings a unique perspe...