How Shopify's Head of Engineering Thinks About His Job And AI - Farhan Thawer

Farhan Thawar leads engineering at Shopify — roughly 3,000 people building the infrastructure behind one of the largest commerce platforms in the world. He joined in 2019 when Shopify acquired Helpful.com, the company he co-founded, and he's been there now for longer than any job he's held before.

This conversation for the StartWell Podcast moves fast, starting with a rapid-fire round before digging into all sorts of great topics and Farhan gives us his take on AI vs. headcount, the most overrated skill in engineering right now, the one line he'd delete from every job posting.

From there, we get into how Shopify actually operates: why they build almost everything in-house, including their own alternative to Jira, why "infrastructure over features" is the default answer to nearly any product decision, how Sidekick, their AI tool, is changing what merchants can do without a developer... And why Farhan thinks most CTOs still have AI's job description wrong - treating it as a cost-cutter when it's really a ceiling-raiser.

We also cover how Shopify runs culture at scale: 1,000 engineering interns a year, a 7,000-person hackathon (the largest in the world) and a philosophy he calls "heightening the misalignment," which is really just a case for being upfront about what kind of company you are.

And underneath all of it is Farhan's own founder story: three pivoted products in three years at Helpful.com, the acquisition, and a still-active habit of angel investing across 106 companies, less for the returns than to stay close to the people building things.

CHAPTERS 00:00 Cold Open: AI vs. People Rapid Fire 03:31 Meet Farhan Thawar, Shopify's Head of Engineering 08:30 Sidekick: Shopify's AI Co-Founder for Merchants 14:30 Inside StartWell's Shopify-Powered Booking System 17:30 Why You Should Re-Test AI Tools Every Few Months 26:00 Build Infrastructure, Not Features 41:00 GSD: Why Shopify Doesn't Use Jira 51:00 The Trust Battery: Making Remote Culture Work 1:09:00 1,000 Interns and the World's Biggest Hackathon 2:04:00 Canada, Build Canada, and Backing 106 Startups