Cartwheel is hiring a Senior Software Engineer to join its AI-first engineering team and help build technology that connects students, families, therapists and schools. The position is fully remote within the United States and offers a salary of $170,000–$200,000 plus meaningful equity.
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About Cartwheel
Cartwheel is a technology-enabled mental health company focused on improving mental health support for children and young people by putting schools at the center of care.
The company works with school staff, clinicians, families and students to enable earlier intervention, stronger engagement and better coordination among the trusted adults supporting students.
For the Senior Software Engineer, this means building products that have a direct impact on how students and clinicians access and experience mental health services. Cartwheel describes the role as an opportunity to work in a Series B environment that is established enough to operate across school districts while still giving engineers significant ownership.
Role Overview
Cartwheel is looking for a product-focused senior engineer who can take ownership of features from architecture through production.
Job Title: Senior Software Engineer
Company: Cartwheel
Job Location: Remote, United States
Employment Type: Full-time
Contract: W2, salaried position
Salary: $170,000–$200,000 + meaningful equity
Work Arrangement: Fully Remote
Experience: 5+ years of professional software engineering experience
You will work as part of a full-stack engineering team of approximately 5–6 engineers and contribute to technical decisions, product development, system reliability and engineering practices.
The role is particularly suited to engineers who care about both technical quality and user outcomes. You may work directly with clinicians, school staff and care teams to understand how the product is being used and turn those insights into improvements.
Cartwheel also operates as an AI-first engineering team, incorporating AI agents and AI-assisted development into everyday engineering workflows.
Key Responsibilities
Technical Leadership and Architecture
You will:
- Lead and contribute to technical design and architecture decisions.
- Evaluate technical trade-offs and communicate recommendations to stakeholders.
- Break complex product and technical objectives into actionable engineering work.
- Help establish scalable architectural patterns and engineering standards.
- Contribute to long-term technical strategy.
Full-Stack Software Development
The role involves:
- Building features across frontend and backend systems.
- Working with React, TypeScript, Hotwire and Ruby on Rails.
- Owning projects from initial planning through production deployment.
- Writing maintainable, well-tested and documented code.
- Participating in code reviews and helping improve engineering practices.
Engineering Quality and Reliability
You will also:
- Develop testing strategies and improve software quality.
- Strengthen monitoring and deployment practices.
- Help identify and address technical debt.
- Contribute to system-health metrics.
- Participate in post-mortems and follow up on corrective actions.
- Improve developer tooling, testing infrastructure and AI agent skills.
- Participate in engineering on-call responsibilities.
Cross-Functional Collaboration
The successful candidate will work closely with:
- Product managers
- Designers
- Clinicians
- School staff
- Care teams
- Operations teams
You will translate user needs into technical solutions and communicate complex technical concepts to non-technical stakeholders.
Required Qualifications
Cartwheel is seeking candidates who have:
- At least 5 years of professional software engineering experience.
- A proven record of delivering high-quality, scalable software.
- Strong full-stack development experience.
- Experience with or willingness to learn Ruby on Rails, Hotwire and React/TypeScript.
- Experience with system design, web application architecture and API design.
- Strong analytical and debugging skills.
- A commitment to testing and maintainable software.
- Strong product engineering instincts.
- Experience using AI-assisted development tools.
- The ability to work independently and take projects from conception through completion.
- Strong written and verbal communication skills.
Additional Experience That Is an Advantage
Cartwheel considers the following experience valuable:
- Healthcare technology experience.
- Mental health technology experience.
- Education technology experience.
- Experience working with regulatory requirements or sensitive user data.
- Early-stage startup experience.
- Developer tooling or engineering infrastructure experience.
- Technical mentorship experience.
- Open-source contributions.
- Technical writing or conference presentations.
AI-First Engineering Environment
Cartwheel emphasizes an AI-first approach to software engineering.
Engineers are expected to consider how AI can improve both development workflows and the products they build. AI agents, architecture documentation, evaluation processes and engineering guidance are incorporated into the team’s development environment.
The company is looking for engineers who are interested not only in using AI tools but also in continuously questioning what can be automated, improved or eliminated to make engineering teams more effective.
Salary and Benefits
The Senior Software Engineer position offers:
- $170,000–$200,000 annual salary
- Meaningful equity ownership
- Fully remote work within the United States
- Flexible working arrangements
- Generous PPO medical, vision and dental coverage
- Paid time off
- Paid parental leave
- 401(k) with employer match
- Annual learning stipend
- Company-provided MacBook
- Regular in-person team retreats
The advertised salary range and remote U.S. arrangement are also reflected in current job listings for the position.
Why Join Cartwheel?
This opportunity is designed for engineers who want their technical work to have a meaningful real-world impact.
Rather than building software in isolation, the Senior Software Engineer will have opportunities to work directly with the people using Cartwheel’s platform and understand how technology can improve workflows for clinicians, schools, students and families.
The role also provides substantial ownership in a growing company, combining senior-level technical responsibility with the opportunity to influence engineering practices and product direction.
How to Apply
Interested candidates should apply through Cartwheel’s official application process.
Note: The position is remote but is limited to candidates based in the United States. The stated start date is September 2026.
Important Recruitment Information
Cartwheel states that it is an equal opportunity employer and welcomes candidates from diverse backgrounds and experiences.
The company also uses AI-assisted tools in parts of its hiring process, while stating that hiring decisions are made by recruiters and hiring managers rather than solely by an automated system.
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