[Your Name] · [Email] · [Phone] · [City, ST]
April 21, 2026
Dear Hiring Manager,
I'm applying for the Senior Product Engineer role on the Checkout Extensibility team. The recent post on the Ruby on Rails monolith's 'Components of Shopify' rollout — and the specific decision to accept compile-time coupling as the price of runtime decoupling — is the kind of pragmatic Rails decision I'd like to be in the room for. At Faire I've been on the other side of that trade-off for two years and I think I'd learn a lot working on the canonical version.
At Faire I led the rebuild of our storefront checkout for 350K+ retailers — the largest dollar-volume change to the Ruby monolith in the company's history. I shipped the first version behind a 1% retailer flag in week 3, not after a quarter of design review, by cutting scope to the single highest-traffic checkout path (US wholesale, credit card only). Over the next 14 weeks I rolled it out retailer-by-retailer, kept the legacy code path live on a feature flag the whole time, and paired weekly with a merchant-success manager who carried the pager for retailer-reported issues. The launch increased completed checkouts by 11.3%, cut retailer-reported checkout bugs by 62%, and the $/month of incremental GMV on the platform crossed $4M by month six. I also run a small Shopify store on the side (a ceramics side-hustle with my partner — about $60K in annual revenue through Shop Pay), which is where I first got frustrated with an API behavior I later realized was the exact thing this team owns.
Before Faire I was employee #22 at a Series A commerce startup (Bold Commerce, Winnipeg) where I wrote the first checkout app on the Shopify App Store and on-called for it alone for 18 months. That range — from 'I am shipping to a Rails monolith with 300 engineers behind me' to 'I am the support queue for 4,000 merchants at 2am' — is the span Shopify's own 'Life Story' interview is designed to surface. I'd rather write code that touches a real merchant's payout than work on anything abstract.
I'd love to talk about the team's current bets on checkout extensibility and the trade-off between merchant customization and core checkout performance. Happy to share the Faire checkout design doc or the App Store app I shipped — whichever is more useful for the loop.
Sincerely,
[Your Name]