Technical Lead - Rails + AI (Remote: LATAM, South Africa, Poland)

About your next team...

JRPass.com sells Japan Rail Passes to travellers around the world.

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  16 year old company based in the UK.

  
  


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  Profitable.

  
  


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  Bootstrapped. No VCs. No investors.

  
  


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  We have a direct commercial partnership with Japan's leading rail operator

  
  


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  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.

Your new role

You will lead our small engineering team of four senior developers.

You will:

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  Write production code every day across Rails and modern JavaScript.

  
  


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  Set how the team uses AI tools (Cursor, Claude Code).

  
  


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  Build our Engineering Health framework. We do not have one yet.

  
  


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  Report directly to our founder-CEO. No long approval chains. You make decisions directly.

  
  

Your first 90 days

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  Audit the codebase. Make it easier for AI to read. Write AGENTS.md files.

  
  


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  Begin careful, AI-assisted upgrades on a 15-year-old codebase. We are not rewriting it from scratch.

  
  


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  Set up a simple Engineering Health framework: flow, ticket quality, knowledge sharing.

  
  


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  Bring commercial thinking to AI tool spending. Companies are reducing AI subsidies. Prices may rise. We need to be ready.

  
  


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  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 of experience matter less than the list below.

You must have:

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  Strong Ruby on Rails experience on live, mature products. Multiple years.

  
  


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  Daily use of Cursor or Claude Code in plan mode. Real practice, not occasional use.

  
  


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  AGENTS.md files you have written. Real examples of making a codebase easier for AI to read.

  
  


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  Strong judgement on live, mature systems. You know when to change a system and when to leave it as it is.

  
  


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  TypeScript and modern JavaScript.

  
  


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  PostgreSQL at production level.

  
  


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  Cloudflare or equivalent edge infrastructure.

  
  


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  The ability to give direct, honest feedback. Even to people who have been there longer than you.

  
  


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  Commercial thinking. You can talk about cost, ROI, and trade-offs.

  
  


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  Discipline to work in a distributed remote team.

  
  

Nice to have:

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  Headless CMS (Strapi, Payload, or equivalent).

  
  


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  E-commerce or travel tech background.

  
  


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  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.


• 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.

 Apply now. We are interviewing every week. No closing date.

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  Flexible working hours with some overlap to UK time.

  
  


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  Long-term security in a profitable bootstrapped business.

  
  

How to apply

Send your CV Apply below or email [email protected] if you'd like more info.

Helen Wingrove-Sanders is the Talent Partner running this search for JRPass.

Fellow recruiters: If you'd like to support this search, please reach out to Helen at HFBAC directly.