I’ve built ecommerce from the inside.
Over a decade building the technology behind online stores, from an entire ecommerce platform to tools used by leading Shopify brands.
I built GrocerKey’s ecommerce platform from scratch as cofounder and CTO, and later served as CTO at PrettyDamnQuick. I know how storefronts, carts, checkout and the services behind them fit together, because I’ve worked on those systems myself.
Experience behind the work
GrocerKey
Cofounder and CTO. Built an ecommerce platform for grocery retailers and led its technology through acquisition.
PrettyDamnQuick
CTO. Worked on checkout and delivery technology serving Shopify brands including Jones Road Beauty, Underoutfit and Laura Geller.
AI consulting
Helping companies apply AI to their products and operations, drawing on extensive experience building and scaling software.
Issues I’ve investigated
These posts document my earlier work on Shopify security, checkout reliability and analytics. They describe what I observed at the time. Some behaviours have since changed.
Security and store visibility
- Exposed inventory data
Reported how outsiders could discover merchants’ exact stock levels without logging in.
- How the inventory exposure worked
Explained the Cart API behaviour and what changed after Shopify introduced quantity limits.
- Gaps in store change history
Highlighted how limited change logs make it difficult to understand what changed in a store.
Checkout reliability
- A connection problem disguised as an address error
Reproduced a checkout failure where losing internet access triggered a misleading shipping address message.
- Checkout timeouts and missing shipping rates
Described shoppers getting stuck and proposed monitoring to detect checkout problems, back in 2024.
- Cart limits that could block real orders
Examined the consequences of automatically applied quantity limits and unclear cart errors.
- Apple Pay checkout limitations
Documented missing shipping descriptions and restrictions in the payment flow, then followed up when the experience changed.
Analytics blind spots
- When “reached checkout” misses shoppers
Investigated discrepancies with a colleague across more than 100 checkouts, comparing the one page and three page flows.
- Checkout clones distorting conversion metrics
Explained how shared checkout links and bots could inflate checkout counts and skew conversion rates.
- Missing addresses in abandoned checkout records
Found that an entered address could appear only as a billing address when shipping rates were unavailable.
- Failed discount codes going unmeasured
Built a checkout extension to capture failed discount attempts and explored the platform limitations around it.
Why I’m building Plainsight
Merchants need to know when something looks wrong, what the evidence shows, and what to do next. Plainsight brings my ecommerce experience to monitoring the storefront your shoppers actually see.