Lenny's Podcast: Product | Career | Growth

Zevi Arnovitz is a product manager at Meta with no technical background who has figured out how to build and ship real products using AI. His engineering team at Meta asks him to teach them how he does what he does. In this episode, Zevi breaks down his complete AI workflow that allows non-technical people to build sophisticated products with Cursor.

We discuss:
1. The complete AI workflow that lets non-technical people build real products in Cursor
2. How to use multiple AI models for different tasks (Claude for planning, Gemini for UI)
3. Using slash commands to automate prompts
4. Zevi’s “peer review” technique, which uses different AI models to review each other’s code
5. Why this might be the best time to be a junior in tech, despite the challenging job market
6. How Zevi used AI to prepare for his Meta PM interviews
—
Brought to you by:
10Web—Vibe coding platform as an API
DX—The developer intelligence platform designed by leading researchers
Framer—Build better websites faster
—
Episode transcript: https://www.lennysnewsletter.com/p/the-non-technical-pms-guide-to-building-with-cursor
—
Archive of all Lenny's Podcast transcripts:
https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
—
Where to find Zevi Arnovitz
• X: https://x.com/ArnovitzZevi
• LinkedIn: https://www.linkedin.com/in/zev-arnovitz
• Website: https://zeviarnovitz.com
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Zevi Arnovitz
(04:48) Zevi’s background and journey into AI
(07:41) Overview of Zevi’s AI workflow
(14:41) Screenshare: Exploring Zevi’s workflow in detail
(17:18) Building a feature live: StudyMate app
(30:52) Executing the plan with Cursor
(38:32) Using multiple AI models for code review
(40:40) Personifying AI models
(43:37) Peer review process
(45:40) The importance of postmortems
(51:05) Integrating AI in large companies
(53:42) How AI has impacted the PM role
(57:02) How to improve AI outputs
(58:15) AI-assisted job interviews
(01:02:57) Failure corner
(01:06:20) Lightning round and final thoughts
—
Referenced:
• Becoming a super IC: Lessons from 12 years as a PM individual contributor | Tal Raviv (Product Lead at Riverside): https://www.lennysnewsletter.com/p/the-super-ic-pm-tal-raviv
• Wix: https://www.wix.com
• Building AI Apps: From Idea to Viral in 30 Days: https://www.youtube.com/watch?v=j2w4y7pDi8w
• Riley Brown on YouTube: https://www.youtube.com/channel/UCMcoud_ZW7cfxeIugBflSBw
• Greg Isenberg on YouTube: https://www.youtube.com/@GregIsenberg
• Bolt: https://bolt.new
• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons
• Lovable: https://lovable.dev
• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika
• StudyMate: https://studymate.live
• Dibur2text: https://dibur2text.app
• Claude: https://claude.ai
• Everyone should be using Claude Code more: https://www.lennysnewsletter.com/p/everyone-should-be-using-claude-code
• Bun: https://bun.com
• Zustand: https://zustand.docs.pmnd.rs/getting-started/introduction
• 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
• Wispr Flow: https://wisprflow.ai
• Linear: https://linear.app
• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu
• Cursor Composer: https://cursor.com/blog/composer
• 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
• Base44: https://base44.com
• Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo
• v0: https://v0.app
• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder & CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch
• Cursor Browser mode: https://cursor.com/docs/agent/browser
• Google Antigravity: https://antigravity.google
• Grok: https://grok.com
• Zapier: https://zapier.com
• Airtable: https://www.airtable.com
• Build Your Personal PM Productivity System & AI Copilot: https://maven.com/tal-raviv/product-manager-productivity-system
• The definitive guide to mastering analytical thinking interviews: https://www.lennysnewsletter.com/p/the-definitive-guide-to-mastering-f81
• AI tools are overdelivering: results from our large-scale AI productivity survey: https://www.lennysnewsletter.com/p/ai-tools-are-overdelivering-results-c08
• Yaara Asaf on LinkedIn: https://www.linkedin.com/in/yaarasaf
• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD
• Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx
• Loom: https://www.loom.com
• Cap: https://cap.so
• Supercut: https://supercut.ai
...References continued at: https://www.lennysnewsletter.com/p/the-non-technical-pms-guide-to-building-with-cursor
—
Recommended books:
• The Fountainhead: https://www.amazon.com/Fountainhead-Ayn-Rand/dp/0451191153
• Shoe Dog: A Memoir by the Creator of Nike: https://www.amazon.com/Shoe-Dog-Memoir-Creator-Nike/dp/1501135910
• Mindset: The New Psychology of Success: https://www.amazon.com/Mindset-Psychology-Carol-S-Dweck/dp/0345472322
—
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.


To hear more, visit www.lennysnewsletter.com

Sam Lessin is a partner at Slow Ventures, a former VP of Product at Facebook, and a two-time founder who’s now teaching etiquette to Silicon Valley’s founders. In this unconventional episode, Sam explains why proper etiquette has become a vital skill for founders in 2026—especially as technology becomes more central to society and trust becomes harder to build. His etiquette book and courses have become surprisingly popular, teaching founders how to “show up in a room with a low heart rate” and quickly build trust.

We discuss:
1. Why etiquette matters
2. Sam’s framework for showing up confidently, with a low heart rate, in any room
3. How to navigate introductions, small talk, meetings, and meals like a pro
4. Simple hacks for remembering names and handling awkward social situations
5. 30+ specific etiquette tips
—
Brought to you by:
10Web—Vibe-coding platform as an API
DX—The developer intelligence platform designed by leading researchers
WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
—
Episode transcript: https://www.lennysnewsletter.com/p/silicon-valleys-missing-etiquette-playbook
—
Archive of all Lenny's Podcast transcripts:
https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
—
Where to find Sam Lessin:
• X: https://x.com/lessin
• LinkedIn: https://www.linkedin.com/in/wlessin
• Website: https://www.wlessin.com
• Podcast: https://moreorlesspod.com
• Lettermeme: https://lettermeme.com/lessin
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Sam’s background
(04:18) The role of etiquette in business success
(09:30) Introductions and entering a room
(16:20) Engaging conversations and building relationships
(23:55) Hygiene and dress code essentials
(33:42) Dining etiquette
(37:15) Tipping etiquette
(41:36) The “B&D trick”
(43:05) Humor in social settings
(45:18) Self-deprecating humor
(47:42) Winding down conversations
(49:20) Scheduling etiquette
(55:23) Communication and email etiquette
(01:02:28) Meeting etiquette tips
(01:04:03) Virtual meeting best practices
(01:05:15) The importance of cleaning up after yourself
(01:05:58) Exiting and follow-up etiquette
(01:07:24) Final thoughts
(01:09:20) AI corner
(01:11:13) Contrarian corner
(01:16:25) Lightning round
—
Referenced:
• Y Combinator: https://www.ycombinator.com
• Kleiner Perkins: https://www.kleinerperkins.com
• “Lose Yourself” by Eminem on Spotify: https://open.spotify.com/track/7MJQ9Nfxzh8LPZ9e9u68Fq
• Alison Gopnik on Childhood Learning, AI as a Cultural Technology, and Rethinking Nature vs. Nurture: https://conversationswithtyler.com/episodes/alison-gopnik
• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan
• Bain & Company: https://www.bain.com
• Evernote: https://evernote.com
• Calendly: https://calendly.com
• Morning Brew: https://www.morningbrew.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
• DigitalOcean: https://www.digitalocean.com
• Cloudflare: https://www.cloudflare.com
• SpaceX: https://www.spacex.com
• Marc Andreessen on X: https://x.com/pmarca
• Landman on Prime Video: https://www.amazon.com/Landman-Season-1/dp/B0D4D8RTMD
• Dave Morin on X: https://x.com/davemorin
—
Recommended books:
• Modern Etiquette in Technology, Finance, Society, and at Home: A Slow Ventures Handbook: https://www.amazon.com/Modern-Etiquette-Technology-Finance-Society-ebook/dp/B0G4HSKSY5
• Life, the Universe and Everything: https://www.amazon.com/Universe-Everything-Hitchhikers-Guide-Galaxy-ebook/dp/B001ODEQ7A
• The Ancient City: A Study on the Religion, Laws, and Institutions of Greece and Rome: https://www.amazon.com/Ancient-City-Religion-Institutions-Greece/dp/0801823048
• Man’s Search for Meaning: https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl-ebook/dp/B009U9S6FI
• Area 51: An Uncensored History of America’s Top Secret Military Base: https://www.amazon.com/Area-51-Uncensored-Americas-Military-ebook/dp/B004THU68Q
• The Lessons of History: https://www.amazon.com/Lessons-History-Will-Durant/dp/143914995X
• The Fish That Ate the Whale: The Life and Times of America’s Banana King: https://www.amazon.com/Fish-That-Ate-Whale-Americas/dp/1250033314
• The Last Kings of Shanghai: The Rival Jewish Dynasties That Helped Create Modern China: https://www.amazon.com/Last-Kings-Shanghai-Jewish-Dynasties/dp/0735224439
—
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.


To hear more, visit www.lennysnewsletter.com

Aishwarya Naresh Reganti and Kiriti Badam have helped build and launch more than 50 enterprise AI products across companies like OpenAI, Google, Amazon, and Databricks. Based on these experiences, they’ve developed a small set of best practices for building and scaling successful AI products. The goal of this conversation is to save you and your team a lot of pain and suffering.

We discuss:
1. Two key ways AI products differ from traditional software, and why that fundamentally changes how they should be built
2. Common patterns and anti-patterns in companies that build strong AI products versus those that struggle
3. A framework they developed from real-world experience to iteratively build AI products that create a flywheel of improvement
4. Why obsessing about customer trust and reliability is an underrated driver of successful AI products
5. Why evals aren’t a cure-all, and the most common misconceptions people have about them
6. The skills that matter most for builders in the AI era
—
Brought to you by:
Merge—The fastest way to ship 220+ integrations: https://merge.dev/lenny
Strella—The AI-powered customer research platform: https://strella.io/lenny
Brex—The banking solution for startups: https://www.brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fs
—
Transcript: https://www.lennysnewsletter.com/p/what-openai-and-google-engineers-learned
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/183007822/referenced
—
Get 15% off Aishwarya and Kiriti’s Maven course, Building Agentic AI Applications with a Problem-First Approach, using this link: https://bit.ly/3V5XJFp
—
Where to find Aishwarya Naresh Reganti:
• LinkedIn: https://www.linkedin.com/in/areganti
• GitHub: https://github.com/aishwaryanr/awesome-generative-ai-guide
• X: https://x.com/aish_reganti
—
Where to find Kiriti Badam:
• LinkedIn: https://www.linkedin.com/in/sai-kiriti-badam
• X: https://x.com/kiritibadam
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Aishwarya and Kiriti
(05:03) Challenges in AI product development
(07:36) Key differences between AI and traditional software
(13:19) Building AI products: start small and scale
(15:23) The importance of human control in AI systems
(22:38) Avoiding prompt injection and jailbreaking
(25:18) Patterns for successful AI product development
(33:20) The debate on evals and production monitoring
(41:27) Codex team’s approach to evals and customer feedback
(45:41) Continuous calibration, continuous development (CC/CD) framework
(58:07) Emerging patterns and calibration
(01:01:24) Overhyped and under-hyped AI concepts
(01:05:17) The future of AI
(01:08:41) Skills and best practices for building AI products
(01:14:04) Lightning round and final thoughts
—
Referenced:
• LevelUp Labs: https://levelup-labs.ai/
• Why your AI product needs a different development lifecycle: https://www.lennysnewsletter.com/p/why-your-ai-product-needs-a-different
• Booking.com: https://www.booking.com
• Research paper on agents in production (by Matei Zaharia’s lab): https://arxiv.org/pdf/2512.04123
• Matei Zaharia’s research on Google Scholar: https://scholar.google.com/citations?user=I1EvjZsAAAAJ&hl=en
• The coming AI security crisis (and what to do about it) | Sander Schulhoff: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis
• Gajen Kandiah on LinkedIn: https://www.linkedin.com/in/gajenkandiah
• Rackspace: https://www.rackspace.com
• The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper
• Semantic Diffusion: https://martinfowler.com/bliki/SemanticDiffusion.html
• LMArena: https://lmarena.ai
• Artificial Analysis: https://artificialanalysis.ai/leaderboards/providers
• Why humans are AI’s biggest bottleneck (and what’s coming in 2026) | Alexander Embiricos (OpenAI Codex Product Lead): https://www.lennysnewsletter.com/p/why-humans-are-ais-biggest-bottleneck
• Airline held liable for its chatbot giving passenger bad advice—what this means for travellers: https://www.bbc.com/travel/article/20240222-air-canada-chatbot-misinformation-what-travellers-should-know
• Demis Hassabis on LinkedIn: https://www.linkedin.com/in/demishassabis
• We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents
• Socrates’s quote: https://en.wikipedia.org/wiki/The_unexamined_life_is_not_worth_living
• Noah Smith’s newsletter: https://www.noahpinion.blog
• Silicon Valley on HBO Max: https://www.hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d
• Clair Obscur: Expedition 33: https://store.steampowered.com/app/1903340/Clair_Obscur_Expedition_33/
• Wisprflow: https://wisprflow.ai
• Raycast: https://www.raycast.com
• Steve Jobs’s quote: https://www.goodreads.com/quotes/463176-you-can-t-connect-the-dots-looking-forward-you-can-only
—
Recommended books:
•  When Breath Becomes Air: https://www.amazon.com/When-Breath-Becomes-Paul-Kalanithi/dp/081298840X
• The Three-Body Problem: https://www.amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032
• A Fire Upon the Deep: https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285
—
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.


To hear more, visit www.lennysnewsletter.com

Molly Graham has worked for some of tech’s most effective leaders, including Mark Zuckerberg, Sheryl Sandberg, Chamath Palihapitiya, and Bret Taylor. Today she leads Glue Club, a community for leaders navigating rapid scale, growth, and change. She’s best known for her “Give away your Legos” framework and her collection of practical mental models for leading through hypergrowth.

We discuss:
1. “Give away your Legos”: a framework for scaling yourself as a leader
2. “J-curves vs. stairs”: the two paths of career growth, and why you should pick the scarier path
3. “The waterline model” for diagnosing team problems (and why you should “snorkel before you scuba”)
4. Six rules for creating effective goals (and aligning everyone around them)
5. Rules of thumb for leading through rapid scale and change
6. Her biggest leadership lessons from Mark Zuckerberg, Sergey Brin, Larry Page, Sheryl Sandberg, and Bret Taylor
—
Brought to you by:
DX—The developer intelligence platform designed by leading researchers
Brex—The banking solution for startups
GoFundMe Giving Funds—Make helping a habit
—
Transcript: https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182877855/my-biggest-takeaways-from-this-conversation
—
Where to find Molly Graham:
• X: https://x.com/molly_g
• LinkedIn: https://www.linkedin.com/in/mograham
• Substack: https://mollyg.substack.com
• Website: https://glueclub.com
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Molly Graham
(04:28) Molly’s background at Google, Facebook, Quip, and CZI
(11:29) The “Give away your Legos” framework
(16:44) Managing your inner monster
(19:49) When not to give away your Legos
(21:28) Embracing a long career
(23:25) The J-curve vs. stairs approach to career growth
(32:00) The gift of knowing yourself
(34:28) Learning to be a professional idiot
(38:30) The waterline model: snorkel before you scuba
(47:16) Six rules for creating strong alignment around goals
(57:15) Rules of thumb for leading through rapid scale
(01:07:49) Investing in high performers vs. low performers
(01:10:54) Lessons from Zuckerberg, Sandberg, and Bret Taylor
(1:21:15) Pivoting from ambition to purpose
(1:26:32) Finding stability in instability
(01:29:44) Final thoughts
—
Referenced:
• Making an impact through authenticity and curiosity | Ami Vora (CPO at Faire, ex-WhatsApp, FB, IG): https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora
• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652
• Elliot Schrage on LinkedIn: https://www.linkedin.com/in/elliotschrage
• Quip: https://quip.com
• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor
• Chan Zuckerberg Initiative: https://chanzuckerberg.com
• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths
• ‘Give Away Your Legos’ and Other Commandments for Scaling Startups: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups
• The Muppets: https://muppets.disney.com
• Sara Caldwell on LinkedIn: https://www.linkedin.com/in/saramcaldwell
• J-Curves vs. Stairs: Two Approaches to Career Growth: https://mollyg.substack.com/p/j-curve
• Forget the corporate ladder—winners take risks: https://www.ted.com/talks/molly_graham_forget_the_corporate_ladder_winners_take_risks
• Chamath Palihapitiya on LinkedIn: https://www.linkedin.com/in/chamath
• Lori Goler on LinkedIn: https://www.linkedin.com/in/lori-goler-6b96921
• Joseph Campbell’s quote: https://www.goodreads.com/quotes/192665-the-cave-you-fear-to-enter-holds-the-treasure-you
• Zevi Arnovitz on LinkedIn: https://www.linkedin.com/in/zev-arnovitz
• Peopling 101: The Waterline Model: https://christinehaskell.com/blog/peopling-101-the-waterline-model
• Introduction to NVC: https://www.cnvc.org/learn/what-is-nvc
• I hate OKRs... and other thoughts about goal setting: https://mollyg.substack.com/p/i-hate-okrs-and-other-thoughts-about
• Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics
• James Clear’s quote: https://www.goodreads.com/quotes/9614600-problem-1-winners-and-losers-have-the-same-goals
• Founder mode: https://paulgraham.com/foundermode.html
• Stripe: https://stripe.com
• Patrick Collison on X: https://www.linkedin.com/in/patrickcollison
• John Collison on X: https://x.com/collision
• Seth Godin’s best tactics for building remarkable products, strategies, brands and more: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products
• Eric Antonow on LinkedIn: https://www.linkedin.com/in/antonow
—
Recommended books:
• The Artist’s Way: https://www.amazon.com/Artists-Way-25th-Anniversary/dp/0143129252
• Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212
• Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones: https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299
—
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.


To hear more, visit www.lennysnewsletter.com

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
—
Brought to you by:
DX—The developer intelligence platform designed by leading researchers
Vercel—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the web
Datadog—Now home to Eppo, the leading experimentation and feature flagging platform
—
Transcript: https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182902716/my-biggest-takeaways-from-this-conversation
—
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
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
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
—
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.


To hear more, visit www.lennysnewsletter.com