SaaStr 818: Anthropic, Cursor, Fal & Bessemer: The Realities of Scaling AI
The Official SaaStr Podcast: SaaS | Founders | Investors
Release Date: 09/05/2025
SaaStr 818: Anthropic, Cursor, Fal & Bessemer: The Realities of Scaling AI
The Official SaaStr Podcast: SaaS | Founders | Investors
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 -...
info_outline
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...
info_outline
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...
info_outline
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...
info_outline
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...
info_outline
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...
info_outline
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....
info_outline
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...
info_outline
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...
info_outline
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...
info_outlineSaaStr 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.
---------------------