Skip to content
Aakash GuptaAakash Gupta

The GitHub Repo That Runs Her $100M Startup

Jiaona Zhang (JZ) is the CPO at Laurel, a $100M AI timesheet platform. She has led product at Airbnb, Dropbox, Webflow, and WeWork. Today she runs a product team that ships front-end and back-end features end-to-end. In this episode, she screenshares Laurel's full Company OS live, walks through the agent pipeline, shows how non-technical team members ship to production using AI, and breaks down the 4 levels of AI maturity she uses to assess every candidate she interviews. Full Writeup: https://www.news.aakashg.com/p/how-to-build-an-ai-native-team Transcript: https://www.aakashg.com/how-to-build-ai-native-team/ Laurel: https://www.laurel.ai/ --- Timestamps: 0:00 - Intro 1:46 - Episode begins 2:04 - The Company OS: GitHub structure screenshare 5:40 - The 1% vs 99% problem 9:00 - 3 steps to build your own Company OS 10:05 - Ads 12:30 - Slack automation demo: feature request triage 14:31 - Playbook to agent pipeline 22:51 - Company culture and the companywide hackathon 29:02 - PMs shipping front-end and back-end features 29:44 - The captain model explained 30:34 - Ads 32:37 - Continuation to captain model 37:38 - Two-track product reviews 50:08 - The AI Ops team and the Sasha model 57:59 - The screen-share interview 59:01 - The 4 levels of AI maturity 1:06:08 - Outro --- 🏆 Thanks to our sponsors: 1. Ariso - Ship AI agents and features faster, with fewer regressions - https://ariso.ai/aakash 2. Bolt - Ship AI-powered products 10x faster - https://bolt.new/solutions/product-manager?utm_source=Promoted&utm_medium=email&utm_campaign=aakash-product-growth 3. Pendo - The #1 software experience management platform - http://www.pendo.io/aakash 4. Product Faculty - Get $550 off their #1 AI PM Certification with code AAKASH550C7 - https://maven.com/product-faculty/ai-product-management-certification?promoCode=AAKASH550C7 5. Customer.io - Send smarter messages using your product data - http://customer.io/productgrowth --- Key Takeaways: 1. Every company has a 1% who are AI-native and a 99% who do not know what to use when. The Company OS closes that gap by encoding the 1%'s workflows into skills that anyone can use when they open Claude. 2. Build the ontology before you build the OS. Map every team's work to categories and tasks first. Color-code what should get more human time vs what gets automated. The OS is built from that work map. 3. Even the friction of going to a different interface kills adoption. A separate agent tool in a new tab will not get used consistently. Deliver skills and automations inside Slack and email, where people already are. 4. When AI adoption is everyone's responsibility, it is no one's responsibility. Dedicate one person full-time to AI Operations. Start with one person who demonstrates value. Every other function will want their own version within months. 5. The Company OS turns a 50-page playbook into a set of agents. Write the playbook first. Then audit it. What requires a human? What can be automated? Build the skill files from what remains. 6. The captain model replaces the handoff chain. Every feature has one owner end-to-end. The captain is whoever has the most critical skill for that feature's hardest problem. 7. PMs at Laurel ship front-end and back-end features. Not just growth experiments or copy changes. Core product features deeply integrated with billing systems and time entry logic. One PM who identifies as a designer shipped one of these end-to-end last month. 8. JZ went from hundreds of reports to 5 PMs and 4 designers. They ship more than ever. Adding people adds coordination cost. In a world where one PM can take a feature from discovery to production in a day, large teams cancel out their own capacity gains. 9. The new PM interview is a screen share. JZ asks every candidate to show their actual screen. In 60 seconds she knows their level of AI skills. 10. The PM fundamentals never changed. Problem space first. Know why and for whom you are building before you build. The speed changed dramatically. What you are supposed to be doing at the heart of it did not. --- 👨‍💻 Where to find Jiaona Zhang: LinkedIn: https://www.linkedin.com/in/jiaona/ Reforge: https://www.reforge.com/profiles/jiaona-zhang Laurel: https://www.laurel.ai/ 👨‍💻 Where to find Aakash: X: https://x.com/aakashgupta LinkedIn: https://www.linkedin.com/in/aagupta/ Newsletter: https://www.news.aakashg.com #productmanagement #aipm #claude --- About Product Growth: The world's largest podcast focused solely on product + growth, with over 200K+ listeners. Subscribe and turn on notifications.

Jiaona ZhangguestAakash Guptahost
Jun 15, 20261h 7mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Inside Laurel’s GitHub-based Company OS powering AI-native execution at scale

  1. Laurel maintains a companywide GitHub repository structured by function (sales, CS, product, etc.) that stores playbooks, “skill files,” and an ontology of work so teams know exactly which AI-enabled procedure to use when.
  2. The system tackles the “1% vs 99%” adoption gap by turning elite individuals’ workflows into shared, discoverable skills and delivering them in the tools people already use (Slack/email) rather than separate AI interfaces.
  3. A practical build path is outlined: start with one tedious workflow automation (e.g., Slack feature-request intake/triage), graduate to playbooks mapped into reusable skills and sub-agents, then consolidate into a routed “mega-agent” and shared company context.
  4. Culture and governance are treated as core infrastructure: leadership-driven expectations, regular company hackathons, transparency channels (e.g., Devin reviewers), ground rules, and a two-track review system balancing speed with strategy/architecture alignment.
  5. The AI-native org model shifts roles toward leaner teams and “captain” ownership, where PMs and even CSMs can ship front-end and back-end changes (with code review and testing responsibilities), and hiring focuses on screen-shared proof of AI maturity.

IDEAS WORTH REMEMBERING

5 ideas

Treat operating knowledge as code: versioned, searchable, and shared.

Laurel stores function-by-function playbooks and skill files in GitHub, making “how we work” auditable and reusable like software. This creates a single source of truth that can be pulled into AI tools as company context.

The real bottleneck is not AI capability—it’s “what to use when.”

JZ frames adoption as a “1% vs 99%” problem: a few power users tinker while most people are unsure which workflow or prompt applies. A curated OS and just-in-time delivery closes that gap by removing choice overload.

Start with one repeated pain, automate the intake, then scale outward.

Their entry-level example is a Slack workflow that standardizes feature-request details, auto-assigns owners, and creates tickets with SLA expectations. This is a low-friction wedge that proves value before attempting a full OS.

Playbooks only matter if they’re executable—convert them into skills and agents.

A 50+ page GTM/CS playbook becomes practical when decomposed into automatable steps (drafting emails, prospect research, RFP responses) implemented as agents. Adoption improves further when a “mega-agent” routes requests to the right sub-agent.

Deliver workflows where people already work; separate AI tools reduce adoption.

Even small interface switching costs (going to an agent builder) can kill usage. Laurel emphasizes Slack/email delivery and Claude skill files embedded in org context so actions are invoked in-flow, not in a separate destination.

WORDS WORTH SAVING

5 quotes

You got these people who are these 1% AI users. They're highly AI-pilled. And then you have the, you know, 90 to 99% of the rest of the organization who isn't sure what to use when.

Jiaona Zhang

The big learning that we've had is how do you create a wrap, like a, like a mega agent, something like the f- like a, um, a go-to-market agent that can be called by the sales team at any point, by the success team at any point, and then that agent is able to route the ask, the, the need, or the help to whatever one of these sub-agents that is actually useful.

Jiaona Zhang

I think the first, uh, advice I'd give is transparency is everything.

Jiaona Zhang

But I, I really don't believe in this, I think a lot of, quote-unquote, "AI-native companies" are just like, "Roadmaps are gone, plannings are gone, everything is gone." Um, and what I say is, well, if everyone's running in different directions, even if you're running incredibly fast, you're not really gonna get anywhere.

Jiaona Zhang

The fundamentals and the principles have never changed. In fact, they're even more important than ever before. But the tools and the way you operate, and the way you, um, can blast through the bureaucracy and feel empowered, that's radically changed.

Jiaona Zhang

GitHub as Company OS (folders by function)Ontology/work maps for each functionSkill files in Claude/company contextSlack automation for feature request intake + triagePlaybooks → agents → routed “mega-agent”Captain model for initiative ownershipTwo-track product reviews (fast lane vs strategy/architecture)PMs/CSMs shipping with Devin + code reviewAI Ops team as “new BizOps” (the “Sasha model”)Interviewing via screen share; four levels of AI maturity

High quality AI-generated summary created from speaker-labeled transcript.

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.