Senior Software Engineer

Join Cartwheel to Help Tackle the Student Mental Health Crisis

Cartwheel is an early-stage company building a new kind of mental health program for kids that puts schools at the center. We see our role as supporting school staff who see kids every single day. Instead of going around them, we collaborate with them. This means:

• Earlier intervention
• Higher student and family engagement in care
• Better coordination among the trusted adults in a student's life

Kids shouldn't just aspire to get out of bed and drag themselves to class. They should be able to experience joy. They deserve to envision and build a life they're excited to live. If you join Cartwheel, you'll help make this vision a reality for millions of students across the country. We're backed by top investors including Menlo Ventures, Reach Capital, General Catalyst, BoxGroup, and Able Partners, and we're looking for mission-driven teammates to join our team.

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. This is a company that's large enough to be real (Series B, operating in districts across the country) and small enough that your pull requests are not invisible. 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. You should also be comfortable working as a forward-deployed engineer, sitting with clinicians, school staff, and our care team, watching them use what we built, and turning what you see into shipped changes quickly. The industries we work in, healthcare and education, haven't historically moved fast on technology. That's the opportunity, not the constraint.

How We Work: AI-First

We are an AI-first engineering team, and we mean it as a practice rather than a slogan. Agents are part of our day-to-day toolchain, and the context that makes them effective, styleguides, agent skills, architecture docs, evals, lives in the repo and is maintained like any other code. We expect engineers to keep asking what should be automated, what should be deleted, and where AI can raise the quality or speed of our work, in our own workflows and in the product itself. If you're the kind of engineer who is constantly rethinking how the work gets done instead of just doing more of it, you'll fit here.

What You'll Do

Technical Leadership & Architecture

• 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
• Contribute to technical standards and architectural patterns that will scale with the organization's growth

Full-Stack Development & Delivery

• 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

Quality & Engineering Excellence

• 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 — improve review tooling, test reliability and speed, and the agent skills the whole team depends on, so everyone's output gets better
• Champion software quality by implementing testing strategies, monitoring solutions, and deployment practices that ensure system reliability
• Contribute to technical debt management by identifying areas for improvement and proposing pragmatic solutions that balance short-term needs with long-term sustainability
• 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
• Invest beyond your own tickets: act as a self-starter rather than an adopter by spotting gaps and opportunities without waiting to be assigned
• Invest in engineering health beyond your immediate work: build internal tools that make the team faster, speed up tests and builds, improve tooling and agent skills, and clean up the systems others rely on
• Support new hire onboarding and contribute to a culture of learning through talks, content, or workshops
• Serve as engineering on-call to help identify, triage, and resolve issues beyond your own team's surface area

Cross-Functional & Forward-Deployed Collaboration

• 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, to understand their workflows firsthand and close the loop quickly on what you learn
• Communicate technical concepts effectively to non-technical stakeholders, ensuring alignment between engineering capabilities and business objectives

Who You Are

Must Have...

• 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, and you're comfortable being forward-deployed with the people who use what you build
• 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

Extra Credit...

• Healthcare, mental health, or education technology experience with understanding of regulatory requirements and user sensitivity
• Early-stage startup experience with ability to work effectively in fast-paced, evolving environments
• Technical mentorship experience with a track record of helping other engineers grow their skills
• Open source contributions or technical writing that demonstrates your expertise and communication abilities

Why You'll Love Cartwheel

Our hope is that Cartwheel will be your best career decision! In addition to tackling one of the biggest challenges of our time, at a company well-positioned to do so, you'll have:

• Mission-oriented and inclusive colleagues who will go to bat for you
• 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