Lenny RachitskyModify

2026-01-01 21:31:28

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

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

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.

My biggest takeaways from this conversation:

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2025-12-30 00:03:32

Here’s a weekly recap of new podcast episodes across Lenny’s Podcast Network:

Every Monday, host Claire Vo shares a 30- to 45-minute episode with a new guest demoing a practical, impactful way they’ve learned to use AI in their work or life. No pontificating—just specific and actionable advice.

How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption

Brought to you by:

• Graphite—Your AI code review platform

• Atlassian for Startups—From MVP to IPO

Rachel Wolan, CPO at Webflow, walks through how she built her own AI chief of staff to run her week—prepping for meetings, auditing her calendar, triaging email, and giving her brutally honest feedback. Claire and Rachel dig into why building personal AI software is the fastest way for executives to really understand what’s possible with AI, how “builder days” can drive org-wide adoption, and why treating software as disposable is a superpower.

Biggest takeaways:

1. The most important outcome is seeing what’s possible. The most heartwarming feedback from Builder Day participants was that it was “eye-opening”—people didn’t understand what was possible until they tried it themselves. Rachel calls this “getting blue-pilled,” when people suddenly step into a new part of their professional journey.

2. Personal software can be ephemeral and imperfect. Rachel builds for an “N of 1” (herself), which allows for hyper-customization. She creates widgets for specific needs (like Q4 roadmap planning) that can be tossed away when no longer needed. This approach treats software as being as accessible as documents: build it, use it, discard it when done.

3. Markdown files are the perfect knowledge base for personal AI. Rachel stores everything from dinner research to product documentation in markdown files, making them easily accessible to both her web app and any LLM she uses. This creates a personal knowledge graph that improves all her AI interactions.

4. Effective AI adoption requires both top-down mandates and bottom-up enthusiasm. Rachel tells her team, “You can’t get into a meeting with me without a prototype,” creating clear expectations. But she also nurtures grassroots enthusiasm through Builder Days, prizes, and recognition.

5. Calendar delegation is a key executive use case. The AI analyzes Rachel’s calendar and suggests which meetings she can skip, delegate, or make asynchronous, even drafting the delegation messages she can send. This reduces the friction of managing time and helps her focus on high-impact work.

▶️ Listen now on YouTube | Spotify | Apple Podcasts

More shows coming soon. . . 👀
If you’re enjoying these episodes, reply and let me know what you’d love to learn more about: AI workflows, hiring, growth, product strategy—anything.

Catch you next week,
Lenny

P.S. Want every new episode delivered the moment it drops? Hit “Follow” on your favorite podcast app.

2025-12-29 20:03:21

Rachel Wolan, the chief product officer at Webflow, has embraced AI not just as a product leader but as a hands-on builder. A coder since age 16, Rachel has returned to her technical roots by creating a custom AI chief-of-staff application that helps manage her executive workload. In this episode, she demonstrates how she uses personal AI software to prep for meetings, triage her calendar, manage emails, and even get brutally honest feedback about how she’s spending her time.

What you’ll learn:

1. How Rachel built a custom AI chief-of-staff application that integrates with her calendar, email, and more

2. Why building personal software can be a gateway to understanding AI’s capabilities for executives

3. How her AI agents help her prep for podcasts, dinners, and meetings with just-in-time information

4. The technical approach to building personal AI software using markdown files, API tokens, and multiple LLM interfaces

5. How Rachel organized company-wide “builder days” that dramatically increased AI tool adoption across her organization

6. Why she believes executives must lead by example in AI adoption to authentically drive organizational change

Brought to you by:

Graphite—Your AI code review platform

Atlassian for Startups —From MVP to IPO

In this episode, we cover:

(00:00) Introduction to Rachel Wolan

(02:26) Why Rachel started leaning into AI

(06:26) Building an AI chief of staff

(08:17) Prepping for the podcast

(10:00) Rachel’s morning flow with her AI chief of staff

(14:14) Designing a personalized interface with custom note cards

(16:34) Getting “brutal truth” feedback from your AI assistant

(19:34) Email triage and management workflows

(23:31) Prepping for networking dinners and events

(28:18) The result of building an AI chief of staff

(30:09) Organizing “builder days” to drive AI adoption

(35:38) Measuring the impact of AI adoption initiatives

(38:00) Lightning round and final thoughts

Tools referenced:

• Claude: https://claude.ai/

• Claude Code: https://claude.ai/code

• Cursor: https://cursor.com/

• Google Calendar API: https://developers.google.com/calendar

• Gmail API: https://developers.google.com/gmail

• Webflow: https://webflow.com/

• Figma: https://www.figma.com/

• Make: https://www.make.com/

• Hex: https://hex.tech/

Where to find Rachel Wolan:

LinkedIn: https://www.linkedin.com/in/rachelwolan/

X: https://x.com/rachelwolan

Webflow: https://webflow.com

Where to find Claire Vo:

ChatPRD: https://www.chatprd.ai/

Website: https://clairevo.com/

LinkedIn: https://www.linkedin.com/in/clairevo/

X: https://x.com/clairevo

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

2025-12-28 21:31:26

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.

We discuss:

1. Why “extraordinary results demand extraordinary efforts”

2. Why you should deliberately understaff projects, and how to know when you’ve gone too far

3. Matt’s transition from COO to CPO and what surprised him about leading product

4. The “high alpha, low beta” framework for evaluating people, processes, and products

5. When founders should quit their startups (hint: much earlier than VCs want you to)

6. How to fight entropy in your organization through relentless energy and intensity

Brought to you by:

Google Gemini—Your everyday AI assistant

Datadog—Now home to Eppo, the leading experimentation and feature flagging platform

GoFundMe Giving Funds—Make year-end giving easy

Where to find Matt MacInnis:

• X: https://x.com/stanine

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

• Email: [email protected]

Referenced:

• Rippling: https://www.rippling.com

• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman

• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill

• Carvana: https://www.carvana.com

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad

• Inkling: https://www.inkling.com

• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari

• Notion: https://www.notion.com

• Conway’s law: https://en.wikipedia.org/wiki/Conway%27s_law

• Seeking Alpha: https://seekingalpha.com

• Dennis Rodman’s website: https://dennisrodman.com

• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle

• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick

• SPOTAK: The Six Traits I Look for When I’m Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html

• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1

• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits

• New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling

• Workday: https://www.workday.com

• Matic robots: https://maticrobots.com

• Wall-E: https://www.imdb.com/title/tt0910970

• Conviction: https://www.conviction.com

• Mike Vernal on X: https://x.com/mvernal

• Sarah Guo on X: https://x.com/saranormous

• No Priors: https://linktr.ee/nopriors

• Gemini: https://gemini.google.com

• ChatGPT: https://chatgpt.com

• Claude: https://claude.ai

• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier

• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c

• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker

Recommended books:

• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595

• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020

• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557

• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459

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.

My biggest takeaways from this conversation:

Read more

2025-12-28 00:59:19

👋 Hello and welcome to this week’s edition of ✨ Community Wisdom ✨ a subscriber-only email, delivered every Saturday, highlighting the most helpful conversations in our members-only Slack community.

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2025-12-24 10:50:17

Noam Segal, AI Insights Manager at Figma, shares the results from our comprehensive survey of 1,750 product managers, engineers, designers, and founders on how AI is reshaping their work. The findings are striking: more than half of respondents are saving at least half a day per week on their most important tasks. Since the quality of AI tools are improving at breakneck speed, Noam reveals we're watching the early innings of a compounding productivity revolution.

Subscribe now

In this episode, you’ll learn:

• Why 55% say AI has exceeded expectations and how it’s improving work quality

• Which roles are winning with AI (and which are struggling)

• Where the biggest opportunities are

• Which AI tools have product-market fit

• Which AI tool dominates for most roles

• Why engineers prefer specialized tools

• Why 92% report significant downsides to AI tools

• What AI agents need to take off

References:

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