Founding Engineer

The Opportunity There are almost 10 million U.S. students with disabilities and diverse learning needs, and that number is growing every year. Teachers who support these students spend hundreds of hours on paperwork, get no real-time guidance when a student falls behind, and rely on spreadsheets, word docs, and paper logs to manage it all. The system is broken not because teachers lack the capabilities, but because they lack tools built for the job.Waypoint is the AI operating system for special education. Our platform helps teachers draft compliant Individualized Education Programs (IEPs), generate curriculum-aligned instructional resources, track student progress, and produce progress reports, saving tons of time and leading to stronger student outcomes. We're live in our first set of teachers, and the early signal is strong.We're looking for a Founding Engineer to be the technical backbone of this company. Today, our MVP handles initial progress reporting and instruction features. The next phase is building the full IEP workflow: drafting goals, generating higher-quality instructional resources, integrating with the software districts already use, and layering in ML models that can identify when a student is falling behind before the quarterly report reveals it. This isn't a role where you'll be handed a spec. You'll be a thought partner to the founder, shaping what we build, how we build it, and how it evolves as we scale from pilot to hundreds of school districts.Role DescriptionOwn the full technical stack. Architect, build, and ship features across the platform: frontend, backend, data layer, infrastructure, CI/CD, testing, monitoring, deployment, and security practices. You are the engineering team until we grow one together, and the practices you establish now will serve the company as it scales.Design and implement AI/ML systems that are the core of the product. This includes LLM-powered workflows, experimentation with agents, and traditional ML techniques for student progress modeling, pattern detection, and outcome prediction.Build integrations with the Student Information Systems (e.g., PowerSchool, Frontline) and supplemental learning tools that districts already use. This means working with APIs, file-based data exchanges, and sometimes messy, legacy technology integrations.Partner with the founder on product direction. Translate teacher feedback and pilot data into technical decisions. Help determine what to build next and how to balance speed with quality.Work directly with pilot teachers and district administrators to understand their workflows, debug issues in real time, and develop empathy for the people we serve.Help recruit and eventually lead the engineering team as we grow. The culture and standards you set now will shape who wants to join us.QualificationsSoftware engineering experience (no set number of years), with meaningful time spent building products end-to-end, not just maintaining features in a large codebase. Startup or early-stage experience is a strong plus.Hands-on experience with LLMs and agentic AI workflows in production. You've built systems that incorporate language models to do real work. You understand prompt engineering, retrieval-augmented generation, orchestration patterns, and the practical challenges of deploying LLM-based systems reliably.Solid foundation in machine learning beyond LLMs. Our platform will use traditional ML for outcome modeling and recommendation systems. Familiarity with supervised learning, time-series analysis, or educational/behavioral data is valuable.Full-stack engineering ability. You're comfortable building responsive frontends, designing APIs, managing databases, and deploying to cloud infrastructure. We care more about your ability to learn and ship in new environments than mastery of any specific language or framework.A product-oriented mindset. You think about the user, and you know how to solicit and prioritize user feedback. You have opinions about what makes a great interface, and you're comfortable making product tradeoffs alongside a non-technical founder.Clear, direct communication. You can explain technical decisions to non-technical stakeholders and you're comfortable being transparent about what's working and what isn't.Nice to HaveExperience in EdTech, Healthcare, or another regulated domain where compliance, data privacy, and user trust are central to the product.Familiarity with K-12 education systems, including how districts procure software, how teachers actually work day-to-day, or how Individualized Education Plans (IEPs) function.Experience with FERPA, COPPA, or similar student data privacy regulations.Experience building API integrations with third-party systems, especially ones with imperfect documentation or legacy constraints.Prior experience as a founding or very early engineer at a startup that went on to raise and scale.CompensationThis role offers an engineering salary reflecting our early stage, paired with a significant founding equity grant. The equity package is designed to reflect the outsize impact this role will have on the company's trajectory and our hope for a long-term commitment to the company. We're open to discussing the specific balance of cash and equity based on your priorities. Benefits details will evolve as we grow, but we're committed to building a sustainable working environment from the start.How to Apply Send an email to Isaac at isaac@waypoint-learning.org with a few sentences about why this role interests you and attach your resume. If you've built something you're proud of – a side project, an open-source contribution, a product you shipped – we'd love to see it. No cover letter required.