Sr. Software Engineer, Ruby on Rails

Location: Remote - US

Department: Engineering

Key Accountabilities: 

• Help shape technical direction on the Essentials squad — contributing to architecture decisions and unblocking teammates — while staying hands-on in Ruby on Rails, TypeScript, and React 

• Lead by example in the codebase: write clean, maintainable, refactor-friendly code and elevate quality through thoughtful code review and pairing 

• Design and optimize back-end systems, APIs, and data flows with a strong focus on performance and reliability, sharing what you learn along the way 

• Build modern, responsive front-end experiences using React, TypeScript, and CSS, with an eye toward maintainable architecture 

• Work across relational databases (Postgres, MySQL, etc.), writing efficient SQL and shaping data models that support business growth 

• Lead projects end-to-end, balancing hands-on development with guiding others to successful delivery, surfacing risks early and communicating trade-offs clearly 

• Collaborate cross-functionally with product, design, and QA to translate business needs into sound technical solutions 

• Embrace AI-assisted engineering: use tools like Claude Code and GitHub Copilot effectively, contribute to shared prompts and agentic workflows, and help the team learn what works 

• Identify and prototype opportunities to apply LLMs and automation to engineering and internal workflows, with the guardrails appropriate to healthcare data and regulated billing 

 

Desired Skills and Experience: 

• At least 7-10 years of full-stack development experience, with Ruby on Rails as a core strength 

• Experience with React, 5+ years preferred. 

• Experienced in leading projects end-to-end: from breaking down complex problems to shipping features that drive impact 

• Passionate about mentoring, from pair programming to guiding architectural decisions, and helping others grow as engineers 

• Daily, hands-on fluency with AI development tools (e.g., Claude Code, Cursor, Copilot), with sharp judgment about where AI accelerates work and where human review is non-negotiable 

• Experience, or strong demonstrated interest, in building with LLM APIs: prompt design, evaluation, and safety considerations for sensitive data 

• Highly organized with superb attention to detail 

• Strong project management skills: comfortable with planning, estimation, and scoping 

• Proven ability to work in an ever-changing environment, ability to connect the dots and make decisions on your own feet 

• Ability to produce quality materials within tight timeframes and simultaneously manage several projects 

• Ability to communicate clearly and concisely, verbally and in writing 

• Exercise sound judgment and work successfully with all employee levels, regardless of background and perspectives 

• Be comfortable working in a distributed, semi-virtual environment 

• Be capable of creating and executing on technical direction and tasks for yourself and others 

• Be able to take minimal direction from others and provide maximal output for yourself (and others)