WhoBuilt

How to Advance Your Career Without Managing People

May 25, 2025· 41 min· 2.9K views·Watch on YouTube
#Organizational Design

Speakers

Sam Gregg-WallaceVP of Talent at Shopify
Peter

Sam Gregg-Wallace, VP of Talent at Shopify, talks with Peter Yang about advancing careers through craft, Shopify’s Mastery System, AI adoption, and reducing workplace distractions.

Reward craft without requiring management

Shopify aims to make individual contributors as important as managers, so people can gain recognition, responsibility, and rewards by deepening their craft. Its Mastery System tracks each person’s impact and skills against role-specific examples of excellence, with promotions and new responsibilities tied to that progress.

Align work and reviews with the mission

Gregg-Wallace says Shopify uses founder-set themes tied to its mission rather than an OKR-driven system. Its GSD tool links projects to those themes and makes work visible. In the Mastery Cycle, employees provide brief reflections and peer feedback, while managers calibrate performance and allocate rewards.

Give employees choice in rewards

Employees who earn a promotion can unlock a title and use Shopify’s Flex Comp rewards wallet. They can choose how much compensation comes as cash or equity, select options or RSUs, and direct some rewards to Shop Cash or carbon removal.

Make AI use part of everyday work

Gregg-Wallace describes AI fluency as an expectation for each employee. Shopify provides a chat surface for available models and embeds Cursor, Copilot, and Claude in development environments; almost two-thirds of its engineers use Cursor daily. Teams share experiments in Slack channels, alongside a prompt library and internally built agents.

Reduce distractions so teams can build

Shopify’s HR team limits interruptions and uses brief patch notes to communicate career-related changes. The company’s operating system encodes principles, connects projects to mission themes, and is designed to make planning more testable and reduce political processes. Gregg-Wallace’s advice is to focus on mission, reward craft, and clear obstacles to shipping for merchants.

Takeaways

  • Build advancement paths that let individual contributors earn responsibility and rewards without becoming managers.
  • Define excellence with role-specific evidence of impact and craft skills.
  • Connect project proposals to a small set of clear company themes.
  • Give employees flexibility in how they receive compensation when the system allows it.
  • Make AI tools accessible in everyday workflows and encourage teams to share practical examples.

Mentioned in this talk

ShopifyCursorGSDShop CashFlex CompMicrosoft CopilotClaudeMastery SystemTobi LütkeJulia

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What was claimed 12

  • uses
    Shopify uses Cursor
    “We see almost two-thirds of our engineers using Cursor every single day.”
    YouTube
    Unverified1 source· Talk
  • role at
    Sam Gregg-Wallace is VP of Talent at Shopify
    “My guest today is Sam, VP of Talent at Shopify.”
    YouTube
    Unverified1 source· Talk
  • founded
    Tobi Lütke founded Shopify
    “it was founded by Tobi”
    YouTube
    Unverified1 source· Talk
  • feature
    Shopify: Career framework evaluates craft and impact and informs promotions, rewards, titles, and responsibilities.
    Career framework evaluates craft and impact and informs promotions, rewards, titles, and responsibilities.
    “all promotions are based on this mastery system”
    YouTube
    Unverified1 source· Talk
  • feature
    GSD: Tracks projects and checks alignment with the company mission and founder-set themes.
    “tracks all of our projects and makes sure they're mission-aligned”
    YouTube
    Unverified1 source· Talk
  • built
    Shopify built GSD
    “We have great homegrown tools, including one called GSD, or 'Get Stuff Done'”
    YouTube
    Unverified1 source· Talk
  • feature
    Shopify: HR and Talent operate in low-distraction mode to reduce interruptions for employees doing product work.
    “All of HR and Talent at Shopify is in low-distraction mode.”
    YouTube
    Unverified1 source· Talk
  • feature
    Flex Comp: Lets employees choose compensation allocation, including equity versus cash and options versus RSUs.
    “select how much equity versus cash they want”
    YouTube
    Unverified1 source· Talk
  • built
    Shopify built Flex Comp
    “This is a very cool thing we've built at Shopify called Flex Comp.”
    YouTube
    Unverified1 source· Talk
  • integrates with
    Shopify integrates with Claude
    “Cursor, Copilot, and Claude are natively embedded here.”
    YouTube
    Unverified1 source· Talk
  • integrates with
    Shopify integrates with Microsoft Copilot
    “Cursor, Copilot, and Claude are natively embedded here.”
    YouTube
    Unverified1 source· Talk
  • metric
    Shopify: Almost two-thirds of Shopify engineers use it every day.
    Almost two-thirds of Shopify engineers use it every day.
    “almost two-thirds of our engineers using Cursor every single day”
    YouTube
    Unverified1 source· Talk

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