Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible for everyone. The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. If you want to use your talents to transform healthcare in the United States, come join us!

We’re hiring a Senior Software Engineer to join our Member Experience engineering team — the team that builds the products our members use every day to find care, understand their benefits, submit claims, and manage their health plans.

You’ll work directly with product and design to ship features that make healthcare more accessible, and you’ll use AI tools as a core part of how you build. Build and ship full-stack features end-to-end across our member-facing web applications

Work primarily in TypeScript — it’s our language of choice across the stack

Ship confidently through our GitHub Actions CI/CD pipelines and deploy web applications on Vercel, owning your changes from pull request to production

Design scalable systems and make deliberate architectural tradeoffs between performance, maintainability, and speed to ship

Build AI-powered member experiences — integrating LLM APIs and working with agent harnesses and frameworks (e.g., Write clean, well-tested, production-grade code with a high bar for quality

Partner with product, design, and stakeholders across the business to translate requirements into great software





Contribute to engineering standards through code reviews, technical discussion, and better defaults

5+ years of professional software engineering experience with full-stack ownership of production systems

- Deep TypeScript expertise, with solid React and Next.js experience building modern, responsive web applications
- Comfort owning deployments end-to-end — experience with platforms like Vercel and CI/CD pipelines like GitHub Actions
- Habitual, fluent use of AI tools (Claude, Cursor, etc.) Experience building with LLMs — API integrations, agentic workflows, or frameworks/harnesses such as Eve or Strands — or a strong drive to get there quickly
- Solid fundamentals in system design, testing, debugging, and code review
- Bachelor’s degree in Computer Science or equivalent practical experience

React Native experience for our mobile surfaces

Familiarity with Java — we have some legacy Java services you may occasionally touch, but no Java expertise is needed for this role

Experience with AWS

We prioritize impact over polish. Bias for action — ship, learn, iterate

Ownership — you design it, build it, run it

Competitive salary, bonus opportunity, and equity package

Comprehensive Medical, Dental, and Vision benefits

A 401k retirement plan

Paid vacation and company holidays

Sidecar Health is an Equal Opportunity employer committed to building a diverse team. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status.

📌 Senior Full Stack Software Engineer/Technology (Canada)
🏢 Sidecar Health
📍 Canada