SaaStr 806: How The Smartest Founders Are Already Winning with AI: SaaStr CEO Jason Lemkin on My First Million
The Official SaaStr Podcast: SaaS | Founders | Investors
Release Date: 06/15/2025
SaaStr 835: AI + B2B in 2026: Find the Tailwinds or Get Left Behind with SaaStr CEO and Founder Jason Lemkin
The Official SaaStr Podcast: SaaS | Founders | Investors
SaaStr 835: AI + B2B in 2026: Find the Tailwinds or Get Left Behind with SaaStr CEO and Founder Jason Lemkin Software spend is set to hit record levels in 2026, but you're not getting any of it unless you change. SaaStr CEO and Founder Jason Lemkin breaks down the paradox facing B2B companies right now: It's never been easier to scale to $100M (for a select few), while everyone else struggles. Half of all VC dollars are going into just 4 deals. IPOs ended the year with a whimper. And that AI copilot you built? It doesn't count. In this session, Jason shares the data on what's actually...
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SaaStr 834: Why OpenAI Doesn't Pay Sales Commission (And Why It Works) with OpenAI GTM Leader Maggie Hott, and Harry Stebbings, Founder of 20VC
The Official SaaStr Podcast: SaaS | Founders | Investors
SaaStr 834: Why OpenAI Doesn't Pay Sales Commission (And Why It Works) with OpenAI GTM Leader Maggie Hott, and Harry Stebbings, Founder of 20VC Discover how OpenAI’s unique approach to B2B sales compensation is changing the game. In this interview with Harry Stebbings, Founder of 20VC, Maggie Hott, OpenAI GTM leadership, shares her experience at OpenAI, including why they don’t pay sales commissions, and what B2B sales leaders can learn from this disruptive model. --------------------- This episode is Sponsored in part by HappyFox: Imagine having AI agents for every support task — one...
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SaaStr 833: AI and the Death of the 2021 Sales Playbook with SaaStr CEO and Founder Jason Lemkin
The Official SaaStr Podcast: SaaS | Founders | Investors
SaaStr 833: AI and the Death of the 2021 Sales Playbook with SaaStr CEO and Founder Jason Lemkin Join SaaStr CEO and Founder Jason Lemkin from SaaStr London as we tackle pressing topics in AI and sales during an engaging AMA session. From discussing the evolution of inbound vs. outbound sales to detailing the transformative impact of AI on sales roles and outbound strategies, this session covers it all. Learn about the importance of product expertise for selling AI solutions, the rise of AI SDRs, and why knowing your top three problems is crucial for effective outbound marketing. Plus,...
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SaaStr 832: How to Use AI to Hyper-Customize Go-To-Market at Scale with SaaStr's CEO and Chief AI Officer
The Official SaaStr Podcast: SaaS | Founders | Investors
SaaStr 832: How to Use AI to Hyper-Customize Go-To-Market at Scale with SaaStr's CEO and Chief AI Officer In this episode from SaaStr AI London 2025, SaaStr CEO and Founder Jason Lemkin and SaaStr's Chief AI Officer, Amelia Lerutte discuss the implementation and optimization of AI SDRs within various business contexts. They focus on key AI agents used for sales processes, data aggregation, and the customization of outbound and inbound messages. Real-world results, like increased email response rates, are highlighted along with practical steps for setting up and training AI SDRs. They...
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SaaStr 831: How We Use 20+ AI Agents for Marketing & Go-to-Market with SaaStr's Chief AI Officer and CEO & Founder
The Official SaaStr Podcast: SaaS | Founders | Investors
SaaStr 831: How We Use 20+ AI Agents for Marketing & Go-to-Market with SaaStr's Chief AI Officer and CEO & Founder Join us for part two of our series on leveraging AI tools for Go-To-Market in B2B/SaaS. In this episode, SaaStr's CEO and Founder Jason Lemkin, and SaaStr's Chief AI Officer, Amelia Lerutte discuss the importance and current state of AI in marketing, highlighting their key tech stack and tools. They share their experiences and insights in utilizing these tools for creating personalized marketing collateral, automating content repurposing, and optimizing email...
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SaaStr 830: 6 Months Later, How Our AI SDRs Actually Work as AI Runs GTM with SaaStr's CEO and Chief AI Officer
The Official SaaStr Podcast: SaaS | Founders | Investors
SaaStr 830: 6 Months Later, How Our AI SDRs Actually Work as AI Runs GTM with SaaStr's CEO and Chief AI Officer In this episode, SaaStr CEO and Founder Jason Lemkin and SaaStr's Chief AI Officer, Amelia Lerutte delve into their journey of integrating AI into our go-to-market strategy over the past six months. Starting with just one AI agent before SaaStr Annual in May, we've scaled to roughly 20 core agents by November, covering various use cases across marketing, sales, customer support, and operations. Together they discuss the specifics of our AI implementations, the tools we have deployed,...
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SaaStr 829: A Hands-On Guide to SaaStr's New AI Tools with SaaStr CEO and Founder Jason Lemkin
The Official SaaStr Podcast: SaaS | Founders | Investors
SaaStr 829: A Hands-On Guide to SaaStr's New AI Tools with SaaStr CEO and Founder Jason Lemkin We delve into the functionalities of our SaaStr AI tools, including the AI Mentor, which has been engaged over 100,000 times, providing answers to various startup-related queries. You'll see a demonstration of how our AI VC tools, including a startup valuation calculator, pitch deck analyzer, and benchmarking tool, work effectively to help startups understand their valuations, get honest feedback on pitch decks, and connect with VCs. Additionally, explore our newly launched VC...
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SaaStr 828: The AI Revolution in B2B: Insights from SaaStr CEO Jason Lemkin and SaaStr Chief AI Officer Amelia Lerutte, and Qualified's CEO and Founder Kraig Swensrud
The Official SaaStr Podcast: SaaS | Founders | Investors
SaaStr 828: The AI Revolution in B2B: Insights from SaaStr CEO Jason Lemkin and SaaStr Chief AI Officer Amelia Lerutte, and Qualified's CEO Kraig Swensrud Join Kraig Swensrud, founder and CEO of Qualified, as he sits down with Jason Lemkin, CEO & Founder SaaStr, and Amelia LeRutte, Chief AI Officer at SaaStr. In this insightful discussion, they explore the current landscape of AI in business, including the challenges and opportunities of integrating AI agents into companies. From the importance of training to the pressures of staying ahead in AI adoption, this conversation offers...
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SaaStr 826: Why Only “WTF” Products Can Survive Today with Brett Queener Partner at Bonfire Ventures
The Official SaaStr Podcast: SaaS | Founders | Investors
Brett Queener is Partner at Bonfire Ventures, a $1B AUM seed-stage fund writing $3-4M checks into application software companies. He was employee #70 at Salesforce.com, where he built go-to-market, launched the AppExchange, and helped scale the company from its earliest days. Previously, he worked at Siebel Systems (the fastest-growing software company of its era) and ran a B2B startup (SmartRecruiters) from pre-revenue to $100M ARR. He writes about the changing software industry in real-time at his Substack. He came to for a deep dive on AI and Product. This episode explores the...
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SaaStr 825: The State of AI + Software: Where It’s Going - Fast
The Official SaaStr Podcast: SaaS | Founders | Investors
In this comprehensive session, SaaStr CEO and Founder Jason Lemkin dives into the latest trends and developments in AI, particularly in the go-to-market (GTM) sector. The session outlines how innovative AI tools are transforming businesses, from AI SDRs and BDRs to forward-deployed engineers. Leaders in the industry are pushing the boundaries, showing higher growth rates and superior marketing efficiency. We also discuss the importance of hands-on deployment and training of AI tools to achieve success, and analyze the current and future impact of AI on B2B companies. Tune in for detailed...
info_outlineSaaStr 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 perspective.
Together they discuss various applications of AI in content creation, customer support, and business advice, highlighting unexpected use cases and the potential for AI to surpass human capabilities. Jason also provides a candid look at the future of startups, the challenges of VC investment, and the evolving landscape of tech-driven by AI. Whether you're a startup founder, investor, or tech enthusiast, this episode is packed with valuable lessons and forward-thinking perspectives.
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This episode of the SaaStr podcast is sponsored by: Attio
This episode is brought to you by Attio — the AI-native CRM. Connect your email, and Attio instantly builds a powerful CRM - with every company, contact and interaction you've ever had. Get 15% off your first year at https://attio.com/saastr
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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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