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AI predictions: Job markets, Codex beats Claude, and the death of org charts | Dan Shipper

Dan Shipper is the co-founder and CEO of Every, a media and software company that’s become a living laboratory for the future of work. Everyone at his company of about 30 people is an AI early adopter; from editors to ops people, they use AI to do much of their work, giving Every a unique lens into where the world is heading. A year ago on this show, Dan predicted that people were sleeping on Claude Code for nontechnical work, which proved to be remarkably prescient. Today he’s back with another set of calls: the SaaS apocalypse is dumb, CLIs are over, the forward deployed engineer is the most valuable new hire, and the only thing you need to do to stay employed is ride the models. *Dan’s predictions:* 1. The future of work will happen inside Codex or Claude Code. 2. Every company will have one “super-agent” inside their Slack that every employee talks to regularly. 3. SaaS is not dead—in fact, Dan is bullish on SaaS stocks. His contrarian take: “I would buy SaaS stocks right now.” 4. SaaS economics will shift: users will bring their own AI tokens into apps, which actually improves SaaS margins. 5. PMs will thrive in the AI era. 6. Full-stack designers will become superheroes. 7. The AI job apocalypse is not happening. 8. Forward deployed engineer is the new most essential role. 9. CLIs are over. 10. Automation is a lie. 11. We will read way more AI-generated writing and we will like it. 12. We’ll be building software for humans and agents to use together. *Brought to you by:* WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny Vanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny *Episode transcript:* https://www.lennysnewsletter.com/p/the-ai-paradox-dan-shipper *Archive of all Lenny's Podcast transcripts:* https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 *Where to find Dan Shipper:* • X: https://x.com/danshipper • LinkedIn: https://www.linkedin.com/in/danshipper/ • Podcast: https://every.to/podcast • Website: https://danshipper.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 Dan Shipper (02:56) Dan’s unique position living in the AI future (09:17) How the way we work will change in the coming year (16:39) The case for general agents (18:08) Codex and Claude Code as the new operating system for work (25:39) How Cursor fits in (27:42) How this changes what SaaS companies should build (31:13) Why CLI is already over (33:34) Two agents are better than one (36:22) Why Dan is bullish on SaaS stocks (39:01) Why automation doesn’t reduce human work (47:00) The value of human-written code (48:36) Quick recap (50:15) How work is changing (56:17) Why data scientists are drowning in bad analysis (58:24) Which product/tech roles are least changed by AI (1:02:17) We will read way more AI-generated writing and we will like it (1:08:28) Why product managers will dominate the AI era (1:11:05) Full-stack designers are the other big winners (1:13:11) The AI job apocalypse won’t happen (1:16:00) How to “ride the models” to stay relevant (1:21:02) Final predictions and advice (1:25:24) Lightning round *Referenced:* • 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 • Claude Cowork: https://claude.com/product/cowork • Codex: https://chatgpt.com/codex • Everyone should be using Claude Code more: https://www.lennysnewsletter.com/p/everyone-should-be-using-claude-code • Every: https://every.to • Kieran Klaassen on X: https://x.com/kieranklaassen • Cora: https://cora.computer • Kate Lee: https://every.to/@kate_1767 • METR (Model Evaluation and Threat Research): https://metr.org • OpenClaw: https://openclaw.ai • Shopify: https://www.shopify.com • Ramp: https://ramp.com • Brandon Gell on LinkedIn: linkedin.com/in/brandongell • Proof: https://every.to/on-every/introducing-proof • Devin: https://devin.ai • 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 ...References continued at: https://www.lennysnewsletter.com/p/the-ai-paradox-dan-shipper _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._ Lenny may be an investor in the companies discussed.

Lenny RachitskyhostDan Shipperguest
May 24, 20261h 34mWatch on YouTube ↗

Episode Details

EPISODE INFO

Released
May 24, 2026
Duration
1h 34m
Channel
Lenny's Podcast
Watch on YouTube
▶ Open ↗

EPISODE DESCRIPTION

Dan Shipper is the co-founder and CEO of Every, a media and software company that’s become a living laboratory for the future of work. Everyone at his company of about 30 people is an AI early adopter; from editors to ops people, they use AI to do much of their work, giving Every a unique lens into where the world is heading. A year ago on this show, Dan predicted that people were sleeping on Claude Code for nontechnical work, which proved to be remarkably prescient. Today he’s back with another set of calls: the SaaS apocalypse is dumb, CLIs are over, the forward deployed engineer is the most valuable new hire, and the only thing you need to do to stay employed is ride the models. *Dan’s predictions:*

  1. The future of work will happen inside Codex or Claude Code.
  2. Every company will have one “super-agent” inside their Slack that every employee talks to regularly.
  3. SaaS is not dead—in fact, Dan is bullish on SaaS stocks. His contrarian take: “I would buy SaaS stocks right now.”
  4. SaaS economics will shift: users will bring their own AI tokens into apps, which actually improves SaaS margins.
  5. PMs will thrive in the AI era.
  6. Full-stack designers will become superheroes.
  7. The AI job apocalypse is not happening.
  8. Forward deployed engineer is the new most essential role.
  9. CLIs are over.
  10. Automation is a lie.
  11. We will read way more AI-generated writing and we will like it.
  12. We’ll be building software for humans and agents to use together.

*Brought to you by:* WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny Vanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny *Episode transcript:* https://www.lennysnewsletter.com/p/the-ai-paradox-dan-shipper *Archive of all Lenny's Podcast transcripts:* https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 *Where to find Dan Shipper:*

*Where to find Lenny:*

*In this episode, we cover:* (00:00) Introduction to Dan Shipper (02:56) Dan’s unique position living in the AI future (09:17) How the way we work will change in the coming year (16:39) The case for general agents (18:08) Codex and Claude Code as the new operating system for work (25:39) How Cursor fits in (27:42) How this changes what SaaS companies should build (31:13) Why CLI is already over (33:34) Two agents are better than one (36:22) Why Dan is bullish on SaaS stocks (39:01) Why automation doesn’t reduce human work (47:00) The value of human-written code (48:36) Quick recap (50:15) How work is changing (56:17) Why data scientists are drowning in bad analysis (58:24) Which product/tech roles are least changed by AI (1:02:17) We will read way more AI-generated writing and we will like it (1:08:28) Why product managers will dominate the AI era (1:11:05) Full-stack designers are the other big winners (1:13:11) The AI job apocalypse won’t happen (1:16:00) How to “ride the models” to stay relevant (1:21:02) Final predictions and advice (1:25:24) Lightning round *Referenced:*

...References continued at: https://www.lennysnewsletter.com/p/the-ai-paradox-dan-shipper _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._ Lenny may be an investor in the companies discussed.

SPEAKERS

  • Lenny Rachitsky

    host

    Product advisor and writer/host of Lenny’s Podcast focused on product management and startups.

  • Dan Shipper

    guest

    CEO and founder of Every, writing and speaking about AI, work, and technology.

EPISODE SUMMARY

In this episode of Lenny's Podcast, featuring Lenny Rachitsky and Dan Shipper, AI predictions: Job markets, Codex beats Claude, and the death of org charts | Dan Shipper explores aI work paradox: automation expands work, empowers PMs and designers Work will bifurcate into (1) a company “super-agent” used in Slack and (2) a desktop agent workspace (Codex/Claude Cowork) where most daily work happens inside the agent’s environment.

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