How to Advance Your Career Without Managing People | Sam Gregg-Wallace (Shopify)
Inside Shopify's crafter paradise where ICs can make more than managers, employees advance by mastering their craft, and AI fluency is mandatory
Dear subscribers,
Today, I want to share a new episode with Sam Gregg-Wallace (VP Talent at Shopify).
Sam is building a radical career system where ICs can make more than managers, employees advance by mastering their craft, and AI fluency is mandatory. I’ve been dying to see how all this works and it’s wilder than you think.
Watch now on YouTube, Apple, and Spotify.
Sam and I talked about:
(00:00) Why it’s time to kick down the traditional corporate ladder
(02:00) Shopify's dual career path for crafters and managers
(04:32) Live demo: Why Shopify employees have "mastery points"
(09:07) "Show me the outcome and I'll show you the incentive"
(17:00) Live demo: Employees choose their equity/cash split every quarter
(24:04) She made one video and got hired in 20 hours
(27:36) Driving AI adoption in Shopify after Tobi's AI memo
(32:01) Shopify's "low distraction" mode internal operating system
(39:22) 3 rules to build a crafter's paradise at your company
Shopify’s mastery system to kick down the corporate ladder
Ok let’s get right into it, how is Shopify kicking down the corporate ladder?
Tobi founded the company with a belief that craft is critical for every great product.
So we reject the corporate ladder that forces crafters to become managers just to get ahead.
Instead, we're creating an environment where crafters can focus on what they do best.
You call this the mastery system, right? Can you show us what that looks like?
Sure, let me show you what it looks like from a software engineer’s POV.
There are 3 key elements:
Mastery number: Measures progress in craft combining impact and skills.
Impact tracking: Measures contributions to company, mission, and merchants.
Reward unlocks: Tracks promotions, compensation, titles, and responsibilities.
I love the Pokemon card and gaming motif. Is that by design?
Yes! Your career journey can be both serious and delightful — it can feel a bit like a playing a video game. We try to build all our internal tools to be engaging.
How do you define what "craft" is for different roles?
We start from first principles: What skills does someone need to contribute to our mission and deliver for merchants? Every journey is different, which is why the mastery number approximates the cumulative sum of impact and craft skills.
How do you evaluate PMs using the mastery system? Do you use OKRs?
No, Shopify isn't an OKR-driven company. Instead, Tobi sets a green path for where the company should go which translates into product themes that guide every PM.
The goal is to align all incentives so everyone is working on that green path. It's less about OKRs and more about mission alignment.
Does that mean that PM calibration discussions center around the mission and how much Shopify merchants and users love the product?
Yes, most of what teams deliver is observable. We know who worked on which product and what their impact was. Our homegrown GSD (get shit done) tool tracks all projects and ensures they align with the green path set by our founder.
How do you get your PMs to focus on customers instead of writing internal docs?
That gets right back to craftsmanship. We know that the biggest slowdown is seeking internal alignment instead of just prototyping and shipping code so we try to do the latter as much as possible.
Making performance reviews “low distraction”
Performance reviews and calibrations take up a lot of time. How do you make this process as “low distraction” as possible?
For crafters, we try to minimize their distraction. During our mastery cycle, they just have to answer a few simple questions and then they can get back to work.
For managers, the work is more substantial because that’s core to the craft of management. Managers handle the calibration, write reviews, gather 360 feedback, and make the hard decisions about distributing rewards.
How do you evaluate managers compared to individual crafters?
We consider management a craft in itself.
We want everyone to be as close to the work as possible, but a manager's job is primarily ensuring their team works on the right things at the highest quality level while growing professionally. That's fundamentally different from being an IC.
Shopify's innovative "Flex Comp" system
How does this translate to job titles and compensation? Some people just want the bigger title and more pay.
These are all incentives we think deeply about. When someone performs well, they might unlock a new title and gain access to their rewards wallet through our Flex Comp system.
Our Flex Comp system is unique in that every employee can choose their:
Cash/equity balance. Choose your ideal mix based on personal circumstance.s
Equity structure. Select between options, RSUs, or custom grant structures.
Payout timing. Take compensation quarterly or build longer-term vesting.
Merchant perks. Convert some compensation to ShopCash with a bonus for Shopify merchants
We did this because every employee is at a different life stage. I have recent interns who take minimum salary and maximum equity while others need more cash (e.g., to buy a house). I’ve also seen new parents allocate some money to ShopCash to get discounts on baby gear from Shopify merchants.
That's incredible. I don't think I've seen anything like this anywhere.
Yeah, it's super fun. Every promotion, people can adjust their compensation mix and we're constantly adding new features.
Finding and hiring people who actually give a sh*t
How do you find and reward people who actually care about craft?
The concept of "giving a shit" is undervalued. People who can channel that into everything they do achieve phenomenal outcomes.
It becomes a feedback loop. As we recruit the best crafters who give a shit, they want to work with others who inspire them and also give a shit.
In terms of measuring whether someone gives a shit, we know the products that they work on and their contributions are observable. But there's also whether people are inspired by you and want to work with you. We ask crafters who gives a shit the most and who they'd want to work with on a new project.
Take the example of Julia—she created a marketing video about how she'd add value to Shopify. Within 20 hours, we interviewed and hired her because she gave a shit and showed high agency.
It does seem like high agency people just seem to gravitate to Shopify. I know another intern who got hired after making an parking app. I think it's because you're building for entrepreneurs.
Exactly. Our goal is to reduce complexity for people choosing entrepreneurship. Tobi is engaged with the community because it's his community. Talking to people isn't a chore—it's what we do.
Having worked at many companies, one of my pet peeves is when someone says "I don't own this" or "that's not my team’s problem."
Right. One of our values at Shopify is “act like an owner.” It doesn't matter what your role is—you're part of the company. You're an owner, so act like it.
Making AI fluency mandatory at Shopify
Tobi recently released a memo saying AI usage is now a baseline expectation at Shopify. How did you actually put that into practice?
That memo caught fire because it speaks for itself. What it did was shift responsibility onto every individual to get better and grow. Setting baseline expectations that AI fluency is required means everyone needs to reflexively reach for AI tools.
We're fortunate to have a founder who's a first-mover and always tinkering with the latest tools. He's been building in the open to inspire the company.
Personally, I love the "reflexive" language in the memo because you build reflexes through practice. The biggest beneficiary is Shopify itself—everyone has shifted to taking responsibility for getting better every day with these tools.
But are there any barriers to AI adoption at Shopify? For example, many AI tools aren’t approved internally at many companies.
The barrier to access for AI tools at Shopify is zero.
We've built them directly into our development environments for everyone, not just engineers. We have our own chat surface that has every available model. Cursor, Copilot, and Claude are natively embedded. As a result:
We're seeing almost two-thirds of our engineers using Cursor daily.
When it's built-in and everyone is responsible for using it, adoption explodes.
Do you also have AI training or education programs?
When you say AI training, that sounds pretty corporate to me. Shopify is more of a learner's environment.
I think it's more about building in the open and sharing what you're learning, not mandatory professional development. We also have an internal wiki with a library of prompts and agents that people have built for specific tasks. Nobody builds in secret here—all that knowledge is shared, which raises all boats.
Building a low-distraction work operating system
One of my first interviews was with Kaz (Shopify’s COO) who talked at length about raging against meetings. How else are you reducing distractions for crafters?
We're trying to create the lowest-distraction environment possible so crafters can focus on improving their craft and making an impact for merchants.
We've built an internal operating system for the company that removes distractions from strategic planning and talent management—things that typically slow companies down.
This OS is implemented with engineering thinking rather than traditional HR or operations. It's version-controlled and testable, reducing the need for political planning processes and change management. Together with our mastery system, this lets people spend their creative time focused on building for merchants.
Can you share an example? For example, planning typically takes up a lot of time with multiple management reviews. How does Shopify streamline this?
We start with the mission. From there, our founder Tobi works with product, engineering, and R&D leaders to set themes that go into our internal wiki. Then our "Get Shit Done" (GSD) system requires every new project to connect to those themes.
This approach starts from the mission rather than from "I need this many dollars or people." When you make the most important thing the most important thing, everything else follows.
Three keys to creating a crafter's paradise
Shopify is an 8,000+ person company building a crafter’s paradise. What are your three best tips for companies who want to do the same?
I think there are 3 essential elements:
Mission focus. Shopify's mission is easy to fall in love with: making commerce better for everyone. The longer people are here, the more dedicated they become. Focus energy on the mission instead of on the bureaucracy.
Reject traditional career ladders. We've chosen the unobvious but correct path: prioritizing craftsmanship over management tracks. The best crafters want to work with each other so it’s a virtuous cycle.
Eliminate distractions. Get out of people's way so they can focus on building for merchants. There are only so many hours in the day; you want people focused on what matters.
And of course, attract people who give a shit. They'll find you because the product is magical, the environment is awesome, and the mission is important.
Thanks Sam! I love how opinionated everyone at Shopify is about these values. Hopefully, you can change the culture for the rest of tech too.
Wish more companies value craft and enable their product managers like Shopify!