Senior Rails Developer, Hotwire, Shape-up

Company Introduction
Context is an international travel company, founded in 2003, that champions the transformative power of learning - on the ground and online.
For two decades, we have offered scholar-led tours in 60+ cities worldwide, guided by MA- and PhD-level experts who go beneath the surface to explore art, history, and culture. In March 2020, we launched Context Learning to bring our trademark, expert-guided experiences to online audiences around the world. Our community’s depth of engagement is remarkable. Many customers span multiple generations, underscoring the enduring appeal of our tours. Some families first discovered us when grandparents brought their teenagers two decades ago. Those teenagers are now parents introducing their own children - creating a multi-generational legacy with Context.
Context is sharpening and rebuilding its on-the-ground tours business with a focus on small, expert-led, conversational experiences, so we human beings can advance our capacity to meet across difference - and extend a hand.
Our Team
We’re a tiny, senior-leaning team that ships end-to-end on a modern yet 15+ years old Rails monolith (Rails 8 + Hotwire). We practice Shape Up - from framing to shaping to betting to building and back to framing. You’ll work closely with product (no ticket waterfalls), own meaningful chunk of work across the stack, and watch your work land with real travelers and experts.
We’re remote-first with at least 4 hours of overlap with U.S. Eastern Time. No meetings by default. We pair when it’s useful, write just-enough tests, and practice proof-before-posture: we say it after we’ve shown it in the field.
This Role
We’re hiring a seasoned senior full-stack developer with strong product instincts.

• You’ll join a small, highly productive team building tools that help curious travelers learn through expert-led, in-person experiences.
• You have deep experience with Ruby on Rails as a full-stack framework, plus strong fluency in JavaScript, HTML, and CSS.
• We run a majestic Rails monolith (Rails 8) with Hotwire - enjoying the leverage of a one-person framework.
• We deploy on Heroku via pipelines, use GitHub Actions for CI, and maintain UAT and production environments with a pragmatic testing strategy.

Desired Qualifications

• You’re positive, thoughtful, and compassionate - and a clear writer (or intent on becoming one).
• You’re a self-manager. We shape projects with clear problems and appetites (not ticket waterfalls), and you lead the trade-offs needed to ship.
• You’re product-minded: work isn’t “done” until it lands, is observable, and changes outcomes.
• You contribute technical shaping up front - so product leads can make sound trade-offs and scope projects appropriately.
• You’ve built and maintained production web applications on Ruby on Rails.
• You’ve scaled web applications and maintained high availability and uptime.
• You have a solid grasp of OO design principles.
• You value automated tests and practice TDD where it fits.
• You understand the full web stack - databases (PostgreSQL), background jobs, caching, observability, and performance.
• You’re comfortable with Git and GitHub Flow.
• You’ve built and maintained CI/CD pipelines (we use GitHub Actions + Heroku).
• We’re remote-first. We ask for at least a 4-hour overlap with U.S. Eastern Time (ET).
• We’re a lean team: you’ll ship across the stack, pair when useful, and favor small, end-to-end iterations.

Bonus Points

• You’ve built (or meaningfully explored) Hotwire-based applications (Turbo, Stimulus).
• You’ve contributed to open source.
• You practice - or are open to - pair programming.
• You’re familiar with Shape Up (appetite-based planning, shaped work, bet cycles).

P.S. We welcome applicants from diverse backgrounds. We’re building a global community grounded in curiosity, mutual regard, and respect - diversity matters here.
P.P.S. We’re not able to sponsor visas or work permits at this time.