Senior Software Engineering - Telecommute

Join Cartwheel to Help Tackle the Student Mental Health CrisisCartwheel 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. Earlier interventionHigher student and family engagement in careBetter coordination among the trusted adults in a student's lifeKids shouldn't just aspire to get out of bed and drag themselves to class. 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. 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. How We Work: AI-FirstWe are an AI-first engineering team, and we mean it as a practice rather than a slogan. 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. What You'll DoTechnical Leadership & ArchitectureLead and collaborate on technical design and architecture decisions within your team's domainDrive technical decision-making by evaluating trade-offs, considering long-term maintainability, and communicating recommendations clearly to stakeholdersBreak down complex, high-level product and technical goals into actionable, well-scoped engineering workContribute to technical standards and architectural patterns that will scale with the organization's growthFull-Stack Development & DeliveryDeliver 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 monitoringWrite comprehensive tests and documentation that enable other engineers to understand, maintain, and extend your workParticipate in code reviews, providing constructive feedback that elevates code quality and knowledge sharing across the teamQuality & Engineering ExcellenceDeliver work that is consistently free of critical bugs before it reaches production, and champion best practices on your teamStrengthen 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 betterChampion software quality by implementing testing strategies, monitoring solutions, and deployment practices that ensure system reliabilityContribute to technical debt management by identifying areas for improvement and proposing pragmatic solutions that balance short-term needs with long-term sustainabilityCollaborate on defining meaningful metrics to track system healthParticipate meaningfully in post-mortems and follow through on the action items that come out of themInvest beyond your own tickets: act as a self-starter rather than an adopter by spotting gaps and opportunities without waiting to be assignedInvest 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 onSupport new hire onboarding and contribute to a culture of learning through talks, content, or workshopsServe as engineering on-call to help identify, triage, and resolve issues beyond your own team's surface areaCross-Functional & Forward-Deployed CollaborationPartner closely with product managers, designers, and clinical stakeholders to translate user needs into technical solutionsWork 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 learnCommunicate technical concepts effectively to non-technical stakeholders, ensuring alignment between engineering capabilities and business objectivesWho You AreMust Have...Passion for our mission to tackle the youth mental health crisis and improve outcomes for students and families5+ years of professional software engineering experience with a demonstrated track record of delivering high-quality, scalable solutionsStrong full-stack development expertise with demonstrable ability to build features end to endExperience 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 systematicallySystem design experience that showcases an understanding of web application architecture, API design, and scalable system patternsQuality focus with commitment to writing well-tested, maintainable code that follows established patterns and best practicesProduct 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 buildFluency with AI-assisted development, and genuine interest in improving how a team works rather than only what it shipsSelf-starter mentality with demonstrated ability to take projects from conception to completion with minimal oversightCommunication abilities to collaboratively explain technical concepts to diverse audiencesExtra Credit...Healthcare, mental health, or education technology experience with understanding of regulatory requirements and user sensitivityEarly-stage startup experience with ability to work effectively in fast-paced, evolving environmentsTechnical mentorship experience with a track record of helping other engineers grow their skillsOpen source contributions or technical writing that demonstrates your expertise and communication abilitiesWhy You'll Love CartwheelOur hope is that Cartwheel will be your best career decision! Mission-oriented and inclusive colleagues who will go to bat for youCompetitive compensation between $170,000 - $200,000Generous PPO medical, vision, and dental coverageGenerous paid time off, including company closure from Christmas-New Years (12/25-1/1)Paid parental leave401K with employer matchMeaningful equity ownership stake in CartwheelFlexible and remote role with regular in-person retreatsAnnual learning stipend