Lead the technical evolution of a profitable, bootstrapped product as our next senior Ruby on Rails engineer. This role is central to shaping both the codebase and long-term architecture, with direct influence on product direction and engineering standards. You’ll operate with high autonomy in a remote, asynchronous environment where results and clarity matter most.
What You’ll Do
- Take ownership of the most challenging pull requests—complex features, deep refactors, and performance-sensitive systems
- Improve team output through thorough code reviews that catch edge cases, strengthen security, and uplift overall quality
- Design and implement enterprise-grade capabilities such as SAML, SCIM, audit trails, and fine-grained permissions
- Build and maintain billing infrastructure including subscription logic, usage tracking, and Stripe webhook handling
- Enhance developer experience through tools like API playgrounds, dashboards, and internal workflows
- Develop custom algorithms and backend logic tailored to product needs
- Diagnose and resolve performance bottlenecks using memory and CPU profiling, query optimization, and flame graphs
- Work with native Ruby extensions, C bindings, and compilation challenges when necessary
- Ship polished frontend components using TailwindCSS and TailwindUI with attention to usability and design
- Enforce security best practices by identifying vulnerabilities and reviewing code through a defensive lens
- Stay ahead of advancements in Rails, Ruby, and AI tooling, integrating what delivers lasting value
- Gradually assume oversight of other engineers’ work and guide new technical initiatives
- Make foundational architectural decisions and lead critical projects from concept to deployment
- Gain production access and collaborate on infrastructure using Terraform as responsibilities grow
What We’re Looking For
- Extensive experience building and maintaining production Ruby on Rails applications
- Proven work with Stripe—specifically billing models, subscription lifecycle, and webhook integration
- Strong product intuition—understanding user needs and the purpose behind tasks
- Ability to create clean, functional UIs using modern utility-first CSS frameworks
- Security awareness covering authentication, authorization, and common attack vectors
- Staying current with Ruby, Rails, and ecosystem updates—including practical use of AI tools
- A focus on compounding improvements over short-term fixes
- Proficiency in debugging performance issues across systems and queries
- Clear, concise writing in code comments, documentation, and pull request descriptions
- Self-driven work style—comfortable operating without daily check-ins
- Fluency in written and spoken English
- Degree in Computer Science or a related technical field, or equivalent experience
Nice to Have
- Experience with Terraform for infrastructure management
- Familiarity with AWS services and cloud architecture
- Background scaling systems to handle billions of requests
- Contributions to open-source projects in the Ruby or Rails community
Technology Stack
Ruby on Rails 8.1, Ruby 3.4, Hotwire (Stimulus + Turbo), TailwindCSS, TailwindUI, PostgreSQL, Redis, Sidekiq, Stripe, Terraform, AWS, Cursor, Claude, ChatGPT, Intercom, GitHub, Slack
Benefits & Culture
- Fully remote with async-first communication
- Equity stake in the company
- Profit-sharing model aligned with company success
- Direct collaboration with executive leadership on product and technical vision
- Annual team retreats in inspiring locations
- Transparent, no-politics environment built on trust and ownership
- Emphasis on the "Rails Way"—convention, simplicity, and maintainability
- Support for independent problem-solving—no micromanagement
