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
The Official SaaStr Podcast: SaaS | Founders | Investors
Release Date: 07/02/2025
SaaStr 817: What Happens When AI Kills Your SaaS Growth? Live Q&A with SaaStr CEO and Founder Jason Lemkin
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 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...
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SaaStr 816: PLG to Enterprise to SMB: Insights from Calendly's CEO
The Official SaaStr Podcast: SaaS | Founders | Investors
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...
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SaaStr 815: Redpoint Ventures Playbook: How Top VCs Are Really Investing in AI
The Official SaaStr Podcast: SaaS | Founders | Investors
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...
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SaaStr 814: How to Build Top-Performing Sales Orgs with OpenAI's GTM Leader Maggie Hott
The Official SaaStr Podcast: SaaS | Founders | Investors
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...
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SaaStr 813: From Startup to $11B: ServiceTitan's CRO Breaks Down Their Sales Playbook
The Official SaaStr Podcast: SaaS | Founders | Investors
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...
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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
The Official SaaStr Podcast: SaaS | Founders | Investors
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....
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SaaStr 811: Marketing in the Age of AI with Wiz's CMO Raaz Herzberg
The Official SaaStr Podcast: SaaS | Founders | Investors
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 employed to stand out in the cybersecurity market, the importance of hiring curious and driven...
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SaaStr 810: AI and the Bottom Line, How Canva Turns Freemium into Conversions with Canva's CCO Rob Giglio
The Official SaaStr Podcast: SaaS | Founders | Investors
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 maintaining the company’s unique customer-centric culture. He also discusses the integration of AI to...
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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
The Official SaaStr Podcast: SaaS | Founders | Investors
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 businesses deploying AI agents. Key topics include the distinction between AI agents and assistants, the...
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SaaStr 808: AI and Cybersecurity: Scaling Rubrik to a Billion Dollar Enterprise with Rubrik's Co-Founder and CTO
The Official SaaStr Podcast: SaaS | Founders | Investors
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 resilience, their approach to scaling with multiple product pillars, and their unique use of hackathons to spark innovation. The conversation also delves into customer satisfaction...
info_outlineSaaStr 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 businesses deploying AI agents. Key topics include the distinction between AI agents and assistants, the development of proprietary data models, and the rapid pace of AI adoption. With real-world examples from companies like IBM and Box, this session offers insights into how AI is reshaping software ecosystems, enhancing enterprise capabilities, and potentially redefining market moats.
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This episode of the SaaStr podcast is sponsored by: Attention.com
Tired of listening to hours of sales calls? Recording is yesterday’s game. Attention.com unleashes an army of AI sales agents that auto-update your CRM, build custom sales decks, spot cross-sell signals, and score calls before your coffee’s cold. Teams like BambooHR and Scale AI already automate their Sales and RevOps using customer conversations. Step into the future at attention.com/saastr
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Hey everyone, we just hosted 10,000 of you at the SaaStr Annual in the SF Bay Area, and now get ready, because SaaStr AI is heading to London!
On December 2nd and 3rd, we’re bringing SaaStr AI to the heart of Europe. This is your chance to connect with 2,500+ SaaS and AI executives, founders, and investors, all sharing the secrets to scaling in the age of AI.
Whether you’re a founder, a revenue leader, or an investor, SaaStr AI in London is where the future of SaaS meets the power of AI.
And we just announced tickets and sponsorships, so don’t wait! Head to SaaStrLondon.com to grab yours and join us this December in London.
SaaStr AI in London —where SaaS meets AI, and the next wave of innovation begins. See you there!