Making AI outbound emails high quality

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.

We discuss:

1. How AI is fundamentally changing the sales function

2. Why most SDRs and BDRs will be “extinct” within a year

3. What Jason is observing across his portfolio about AI adoption in GTM

4. How to become “hyper-employable” in the age of AI

5. The specific AI tools and tactics he’s using that have been working best

6. Practical frameworks for integrating AI into your sales motion without losing what works

7. Jason’s 2026 predictions on where SaaS and GTM are heading next

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Transcript: https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents

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My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182902716/my-biggest-takeaways-from-this-conversation

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Where to find Jason Lemkin:

• X: https://x.com/jasonlk

• LinkedIn: https://www.linkedin.com/in/jasonmlemkin

• Website: https://www.saastr.com

• Substack: https://substack.com/@cloud

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Introduction to Jason Lemkin

(04:36) What SaaStr does

(07:13) AI’s impact on sales teams

(10:11) How SaaStr's AI agents work and their performance

(14:18) How go-to-market is changing in the AI era

(19:19) The future of SDRs, BDRs, and AEs in sales

(22:03) Why leadership roles are safe

(23:43) How to be in the 20% who thrive in the AI sales future

(28:40) Why you shouldn't build your own AI tools

(30:10) Specific AI agents and their applications

(36:40) Challenges and learnings in AI deployment

(42:11) Making AI-generated emails good (not just acceptable)

(47:31) When humans still beat AI in sales

(52:39) An overview of SaaStr's org

(53:50) The role of human oversight in AI operations

(58:37) Advice for salespeople and founders in the AI era

(01:05:40) Forward-deployed engineers

(01:08:08) What's changing and what's staying the same in sales

(01:16:21) Why AI is creating more work, not less

(01:19:32) Why Jason says these are magical times

(01:25:25) The "incognito mode test" for finding AI opportunities

(01:27:19) The impact of AI on jobs

(01:30:18) Lightning round and final thoughts

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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

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.