CTO / Senior Developer (part-time, remote)
Way TechnologyWay Labs, St. Louis, Missouri. Part-time, remote (US time zones). We are replacing a 20-year-old e-commerce, warehouse and retail system with a new cloud platform, and we need one senior engineer to be its technical owner: the person who keeps it running, proves it is right, and answers the phone when something breaks. The business behind it is real and busy: several storefronts, two retail stores, a 60,000 square foot warehouse with an automated packing line, Amazon, Walmart and other marketplaces, a 3PL business and a subscription club. Millions of orders of history. How the work is done: most of the code is written by AI coding agents under the owner's direction, and the business rules have been documented module by module. You are not hired to type the code. You are hired to own it: review the architecture, run the data migration, keep the integrations and hosting healthy, and make sure the system is proven correct before each part goes live. You are comfortable working alongside AI agents, reading what they produce, and judging it by tests and evidence, not by eye. What you will do: 1. Review the data model and architecture (a paid trial task to start). 2. Lead the data migration: about 6.7 million orders, 18.5 million lines, customers, stock, gift cards and rewards, from the old Postgres database into the new one. Practice runs, reconciliation to the cent, and a rollback plan. 3. Own the integrations: Amazon, Walmart, eBay, Shopify, Faire; FedEx, USPS and UPS; Square, Braintree and PayPal; TaxCloud; Signifyd. 4. Own the proof: the test suite, the replay of real order history against the old system, and the nightly side-by-side run before cutover. Nothing switches on without passing evidence. 5. Hosting, security and reliability on AWS: backups with tested restores, monitoring and alerts, the web application firewall, and a weekly security review. 6. Technical lead on the switch weekend in January. 7. After go-live: the responsible engineer when the owner is not around, with on-call for real problems. What you bring: 1. 10+ years building and running production systems, ideally e-commerce, order management, warehouse or ERP. 2. Strong Postgres: schema design, large data migrations, performance and row-level security. 3. TypeScript and Node, with React for admin screens. 4. Real experience with carrier, payment and marketplace APIs. 5. AWS (or similar) operations: deployments, backups, monitoring and incident response. 6. Hands-on use of AI coding tools such as Claude Code, and the judgment to verify what they produce. 7. Calm, plain-English communication with a non-technical owner. You say what you checked and what you could not. Nice to have: ColdFusion (the old system), Supabase, Vercel, warehouse automation. Hours and pay: about 10 to 20 hours a week through the January cutover, then about 5 to 10 a week through April, then 2 to 4 a week plus a monthly on-call retainer. $100 to $150 an hour depending on experience, as a contractor. Long-term relationship. To apply: send a short note on the largest data migration you have led and how you proved it was right, plus your experience with AI coding tools. A link to your work or LinkedIn profile is enough; no cover letter needed. Pay: $100.00 - $150.00 per hour Expected hours: 10.0 – 20.0 per week Benefits: Flexible schedule Application Question(s): Describe the largest data migration you have led: the size, where it moved from and to, and how you proved the result was correct. Which of these have you integrated in production: Amazon SP-API, Walmart, Shopify, FedEx, USPS, UPS, Square, Braintree, TaxCloud? Describe one hard problem you solved with one of them. Which AI coding tools do you use today, and how do you check what they produce before it goes live? At 9 PM on Black Friday, the tax service starts failing at checkout. What do you do in the first 30 minutes? How many hours a week can you commit through January, and can you be on call after go-live? Work Location: …