Senior Software Engineer

Role Description

Join Cartwheel to help tackle the student mental health crisis. As a Senior Software Engineer at Cartwheel, you'll build the product that connects students, families, therapists, and schools in real time. You'll work on a full-stack team of 5-6 engineers, owning features end to end — from the architecture decisions that shape how we scale, to the code that goes to production and touches real students and clinicians the next day.

We're looking for a product engineer, not a ticket-taker: someone who cares as much about whether a feature actually works for a school counselor at 8am on a Monday as they do about the code that powers it.

Sometimes that means writing the tool yourself instead of filing the ticket. The industries we work in, healthcare and education, haven't historically moved fast on technology. That's the opportunity, not the constraint.

Qualifications

• Passion for our mission to tackle the youth mental health crisis and improve outcomes for students and families
• 5+ years of professional software engineering experience with a demonstrated track record of delivering high-quality, scalable solutions
• Strong full-stack development expertise with demonstrable ability to build features end to end
• Experience with our technology stack or eagerness to learn: Ruby on Rails, Hotwire, React (TypeScript)
• Problem solving skills with strong analytical and debugging skills and ability to tackle complex technical challenges systematically
• System design experience that showcases an understanding of web application architecture, API design, and scalable system patterns
• Quality focus with commitment to writing well-tested, maintainable code that follows established patterns and best practices
• Product engineering instincts, you think deeply about the user and the business outcome, not just the ticket
• Fluency with AI-assisted development, and genuine interest in improving how a team works rather than only what it ships
• Self-starter mentality with demonstrated ability to take projects from conception to completion with minimal oversight
• Communication abilities to collaboratively explain technical concepts to diverse audiences

Requirements

• Lead and collaborate on technical design and architecture decisions within your team's domain
• Drive technical decision-making by evaluating trade-offs, considering long-term maintainability, and communicating recommendations clearly to stakeholders
• Break down complex, high-level product and technical goals into actionable, well-scoped engineering work
• Deliver high-quality, maintainable, and well-tested code across frontend (React, Hotwire) and backend (Ruby on Rails) needs
• Own and deliver large projects end-to-end, from initial planning through production deployment and monitoring
• Write comprehensive tests and documentation that enable other engineers to understand, maintain, and extend your work
• Participate in code reviews, providing constructive feedback that elevates code quality and knowledge sharing across the team
• Deliver work that is consistently free of critical bugs before it reaches production, and champion best practices on your team
• Strengthen the systems that produce quality rather than only following them
• Champion software quality by implementing testing strategies, monitoring solutions, and deployment practices that ensure system reliability
• Collaborate on defining meaningful metrics to track system health
• Participate meaningfully in post-mortems and follow through on the action items that come out of them
• Act as a self-starter rather than an adopter: spot gaps and opportunities and act on them without waiting to be assigned
• Invest in engineering health beyond your immediate work
• Support new hire onboarding, and contribute to a culture of learning through talks, content, or workshops
• Serve as engineering on-call, and help identify, triage, and resolve issues beyond your own team's surface area
• Partner closely with product managers, designers, and clinical stakeholders to translate user needs into technical solutions
• Work directly with the people using our product, clinicians, school staff, and our care and operations teams
• Communicate technical concepts effectively to non-technical stakeholders

Benefits

• Competitive compensation between $170,000 - $200,000
• Generous PPO medical, vision, and dental coverage
• Generous paid time off, including company closure from Christmas-New Years (12/25-1/1)
• Paid parental leave
• 401K with employer match
• Meaningful equity ownership stake in Cartwheel
• Flexible and remote role with regular in-person retreats
• Annual learning stipend
• Macbook