Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previously handled by a team of 10 SDRs and AEs. In this conversation, Jason shares his hands-on experience implementing AI to run his sales org, including what works, what doesn’t, and how the GTM landscape is quickly being transformed.
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We discuss:
How AI is fundamentally changing the sales function
Why most SDRs and BDRs will be “extinct” within a year
What Jason is observing across his portfolio about AI adoption in GTM
How to become “hyper-employable” in the age of AI
The specific AI tools and tactics he’s using that have been working best
Practical frameworks for integrating AI into your sales motion without losing what works
Jason’s 2026 predictions on where SaaS and GTM are heading next
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Where to find Jason Lemkin:
• LinkedIn: https://www.linkedin.com/in/jasonmlemkin
• Website: https://www.saastr.com
• Substack: https://substack.com/@cloud
Referenced:
• Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org
• SaaStr Annual: https://www.saastrannual.com
• Delphi: https://www.delphi.ai/saastr/talk
• Amelia Lerutte on LinkedIn: https://www.linkedin.com/in/amelialerutte/
• Vercel: https://vercel.com
• What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google): https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently
• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch
• Replit: https://replit.com
• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad
• ElevenLabs: https://elevenlabs.io
• The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack
• Bolt: https://bolt.new
• Lovable: https://lovable.dev
• Harvey: https://www.harvey.ai
• Samsara: https://www.samsara.com/products/platform/ai-samsara-intelligence
• UiPath: https://www.uipath.com
• Denise Dresser on LinkedIn: https://www.linkedin.com/in/denisedresser
• Agentforce: https://www.salesforce.com/form/agentforce
• SaaStr’s AI Agent Playbook: https://saastr.ai/agents
• Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan
• Brian Halligan’s AI: https://www.delphi.ai/minds/bhalligan
• Sierra: https://sierra.ai
• Fin: https://fin.ai
• Deccan: https://www.deccan.ai
• Artisan: https://www.artisan.co
• Qualified: https://www.qualified.com
• Claude: https://claude.ai
• HubSpot: https://www.hubspot.com
• Gamma: https://gamma.app
• Sam Blond on LinkedIn: https://www.linkedin.com/in/sam-blond-791026b
• Brex: https://www.brex.com
• Outreach: https://www.outreach.io
• Gong: https://www.gong.io
• Salesloft: https://www.salesloft.com
• Mixmax: https://www.mixmax.com
• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr
• Clay: https://www.clay.com
• Owner: https://www.owner.com
• Momentum: https://www.momentum.io
• Attention: https://www.attention.com
• Granola: https://www.granola.ai
• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff
• Palantir: https://www.palantir.com
• Databricks: https://www.databricks.com
• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan
• Rippling: https://www.rippling.com
• Cursor: https://cursor.com
• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell
• The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna
• Pluribus on AppleTV+: https://tv.apple.com/us/show/pluribus/umc.cmc.37axgovs2yozlyh3c2cmwzlza
• Sora: https://openai.com/sora
• Reve: https://app.reve.com
• Everything That Breaks on the Way to $1B ARR, with Mailchimp Co-Founder Ben Chestnut: https://www.saastr.com/everything-that-breaks-on-the-way-to-1b-arr-with-mailchimp-co-founder-ben-chestnut/
• The Revenue Playbook: Rippling’s Top 3 Growth Tactics at Scale, with Rippling CRO Matt Plank: https://www.youtube.com/watch?v=h3eYtzBpjRw
• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
Lenny may be an investor in the companies discussed.
