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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 ↗

CHAPTERS

  1. Why Laurel built a company operating system to scale AI use beyond the “1%”

    Aakash introduces Jiaona “JZ” Zhang (CPO at Laurel) and frames the core challenge: a small fraction of employees are highly effective with AI while the majority don’t know what to use when. The episode sets up Laurel’s answer: a company-wide operating system that standardizes workflows, skills, and automation across functions.

  2. GitHub as the ‘Company OS’: folder structure, skills, and cross-functional playbooks

    JZ screen-shares Laurel’s GitHub repo that serves as a company-wide OS. Each function (CS, sales, marketing, engineering, finance, etc.) has structured folders mapping phases of work into repeatable activities and “skill files.”

  3. Making the OS real: Slack-based daily workflows + AI ‘skills’ in company context

    The OS becomes actionable when integrated into where people already work—Slack/email—rather than sitting as documentation. JZ shows how daily briefings and meeting prep connect to skills that can be uploaded into AI tools (e.g., Claude organization skills) for just-in-time execution.

  4. The “1% vs 99%” problem and the ontology mapping of work

    JZ explains how Laurel bridges uneven AI adoption by codifying best workflows from the most AI-native employees and distributing them organization-wide. They map each function’s work into an ontology (categories → tasks) to decide what to automate vs keep human-led.

  5. Three-step blueprint to build your own Company OS (start small → playbooks → agents)

    JZ lays out a progression for companies starting from scratch. Step one is a single tedious workflow automation; step two formalizes playbooks and audits which steps are human vs automatable; step three turns the playbook into agents and skills that run inside daily work tools.

  6. Slack automation demo: feature request intake and triage without back-and-forth

    JZ demonstrates a lightweight but high-leverage starting point: an automated workflow in Slack for feature requests. Instead of long threads, the workflow captures required context (frequency, evidence, impact), routes ownership, and creates a trackable ticket with SLA expectations.

  7. From 55-page playbooks to an agent pipeline (Dust/Claude) and the ‘mega agent’ concept

    JZ shows how large GTM playbooks become actionable by translating steps into agents. She explains why a “mega agent” (e.g., a GTM agent) that routes to sub-agents is more usable than expecting people to remember many specialized tools or commands.

  8. Avoiding automation overload: consolidating scheduled tasks into a single OS experience

    JZ discusses a common failure mode: building too many scheduled automations and overwhelming users with information. Laurel’s OS consolidates skills and automations into a coherent daily experience to keep adoption consistent across roles and proficiency levels.

  9. Culture as infrastructure: company-wide hackathons and ‘everyone is a builder’

    JZ argues the OS only works with the right culture and leadership mandate. Laurel institutionalizes building via recurring hackathons, training, and shared expectations that non-engineers can ship real improvements.

  10. PMs shipping full-stack features with Devin: from onboarding UX to backend changes

    JZ provides concrete examples of PMs shipping production changes, including both front-end and back-end work, using Devin as an agentic engineer. This reframes PM work from coordination-heavy to end-to-end product building with appropriate reviews and safeguards.

  11. The Captain model: ownership based on the hardest thing to get right

    Laurel assigns a “captain” for each initiative based on which discipline is most critical to success (engineering, design, product, data). The model clarifies decision-making while allowing cross-functional contributors to ship with AI assistance and targeted expert review.

  12. Checks, balances, and transparency: code review, shared channels, and compressed collaboration

    Aakash probes how Laurel prevents conflicts, maintains quality, and avoids duplicate work when many roles can ship. JZ emphasizes transparency (shared visibility into shipping), lightweight review channels, and ground rules that compress traditional product reviews into fast, async collaboration.

  13. Two-track product reviews: when to move in hours vs when to do strategy/architecture review

    JZ outlines a two-track review system. Small, end-to-end changes can ship quickly with lightweight review, while systemic interaction changes and strategy shifts require deeper alignment—product strategy review and architecture review—to avoid local optimization.

  14. Scaling the transformation: AI Ops as the new BizOps (‘the Sasha model’)

    JZ explains how Laurel operationalizes AI transformation by dedicating people full-time to building workflows, agents, and efficiencies. An AI Operations team (starting with Sasha) proves value and then expands, creating specialized AI Ops roles per function as demand grows.

  15. Hiring for AI-native builders: screen-share interviews + the four levels of AI maturity

    JZ shares her hiring method: ask candidates to screen share how they actually use AI to distinguish real capability from buzzwords. She defines four levels of AI maturity—from chat usage to workflow automation to app-building to shared apps/shipping—and uses it to assess individuals and organizations.

  16. The future of product orgs: fewer, more senior builders + fundamentals that still matter

    The conversation closes on how AI compresses coordination costs and changes team shapes: leaner product orgs with highly capable, senior product builders. JZ stresses that while tools and operating cadence change dramatically, core product fundamentals—customer-centricity and problem-first thinking—are even more important.

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