Technical Lead - Rails + AI (Remote - Global)
Published on May 11, 2026
JRPass.com helps hundreds of thousands of travellers explore Japan by rail every year. We're one of the largest international sellers of the Japan Rail Pass, and our Rails platform is the engine behind every booking, ticket, and itinerary. Small, remote-first team. Real ownership. Travel-tech that actually ships.
Apply now. We are interviewing every week. No closing date.
About us
JRPass.com sells Japan Rail Passes to travellers around the world.
- 16 years old as a company.
- Profitable.
- Bootstrapped. No VCs. No investors.
- First Western company to sign a formal deal with JR Central, who run the Shinkansen.
- Sister site JapanDen.com is becoming a full Japan travel platform.
Our stack: Ruby on Rails. We are moving to Astro 6 and Strapi for the front end.
The role
You will lead our small engineering team of four senior developers.
You will:
- Write production code every day across Rails and modern JavaScript.
- Set how the team uses AI tools (Cursor, Claude Code).
- Build our Engineering Health framework. We do not have one yet.
- Report directly to our founder-CEO. No long approval chains. You make decisions directly.
Your first 90 days
- Audit the codebase. Make it easier for AI to read. Write AGENTS.md files.
- Begin careful, AI-assisted upgrades on a 15-year-old codebase. We are not rewriting it from scratch.
- Set up a simple Engineering Health framework: flow, ticket quality, knowledge sharing.
- Bring commercial thinking to AI tool spending. Companies are reducing AI subsidies. Prices may rise. We need to be ready.
- Help ship our point-to-point Shinkansen ticket product.
What you bring
You have 8 or more years in production engineering. You have led a small team. Years matter less than the list below.
You must have:
- Strong Ruby on Rails experience on live, mature products. Multiple years.
- Daily use of Cursor or Claude Code in plan mode. Real practice, not occasional use.
- AGENTS.md files you have written. Real examples of making a codebase easier for AI to read.
- Strong judgement on live, mature systems. You know when to change a system and when to leave it as it is.
- TypeScript and modern JavaScript.
- PostgreSQL at production level.
- Cloudflare or equivalent edge infrastructure.
- The ability to give direct, honest feedback. Even to people who have been there longer than you.
- Commercial thinking. You can talk about cost, ROI, and trade-offs.
- Discipline to work in a distributed remote team.
Nice to have:
- Headless CMS (Strapi, Payload, or equivalent).
- E-commerce or travel tech background.
- Knowledge of MCP (Model Context Protocol).
Why this role is different
No investor pressure. 16 years bootstrapped. We are not chasing fast investor returns. We grow steadily.
Real commercial deal. First Western company with a formal agreement with JR Central. Rare.
Direct line to the CEO. No layers. No politics.
Real AI practice. Not a trend. We use AI every day. We also think hard about the risks. In travel, AI agents may start booking trips directly, cutting out websites like ours.
A team ready to be led. Anna (PM), Iasmine (Growth), Caique (SEO Content). All self-directed people who own their work.
Equity is in the plan. Not promised. A direction. Once revenue is steady, equity for the people who help build the business is firmly part of the plan.
Salary (adjusted to your location)
Salary and package is competitive and adjusted for your location. We discuss specifics on the first call.
You also get:
- Flexible working hours with some overlap to UK time.
- Long-term security in a profitable bootstrapped business.
How to apply
Send a CV plus a short note (200 words maximum). Tell us:
- The last codebase you made easier for AI to read. What did you change? What did the team gain?
- The most senior developer you gave hard feedback to. What did you say?
- Why this role? Beyond money.
Apply here on RubyonRemote or email helen@hfbac.com.
Helen Wingrove-Sanders is the Talent Partner running this search for JRPass.