Senior Software Engineer, Data Architecture

Contract or Contract to hire · Remote (U.S.) · 6 month min. contract About Outschool.org Since 2020, Outschool.org has supported hundreds of thousands of families to afford, access and actualize education resources previously out of their reach. Today, Outschool.org builds family navigation tools that help parents find and pay for the education of their dreams. Our state-contracted tools and services currently operate in Arkansas, South Carolina, and Texas. As the number of policies that provide families with access to public funds to purchase educational resources increase, we’re looking to expand from a handful of state contracts to nationwide infrastructure capable of supporting families across the country. The Work We’re looking for a product engineer with focused expertise in PostgreSQL schema design, complex data modeling, and relational database architecture to help build scalable backend tools that serve families, education providers, and state agencies as they navigate learning opportunities enabled by innovations such as Education Savings Accounts (ESAs) and other direct-to-family funding programs. Because our products and services interface directly with public and private infrastructure, you will lead backend integrations across highly configurable, state and program specific workflows. Success in this role will require a candidate who embraces the design challenges native to working on interoperable data systems that reach across both legacy government systems and partner business systems, while collaborating closely on the product interfaces end users touch every day. In this 6 month contract period, daily work will involve partnering with our other senior engineer and product director on these workstreams: 1 . Flagship finder product interoperability. Our flagship product helps parents in ESA eligible states assess educational service and product offerings available to them with their program dollars — from tutors to ju-jitsu classes, or even private school tuition — to make choices that best fit their child’s needs. We offer this service as a delivery partner via private and public-sector partnerships with clients like state departments of education, and the wallet platforms that administer scholarship funds to parents. As our data architecture focused engineer, you’ll help architect improved cross-entity data integration and handling with those partners. This includes owning complex identity management architecture, and puzzles like how best to verify credentials against shifting state criteria. AI-powered compliance tool. An early stage tool to help parents submit reimbursement requests, evaluates them for eligibility against state policy, and helps program administrators review them efficiently. You'd help shape this architecture from the ground up, working with our product team on a staged scope, and ship it. Canonical postgres engine & ETL. Drive our overarching migration from an Airtable-centric data layer to a highly optimized, production Postgres database. Improve our Python ETL pipelines that ingest weekly state data across multiple regions. Beyond these areas, you’ll weigh in on architecture across the stack and support our product portfolio as needed to support our rapidly evolving and exciting work! Skills & Experience Must-haves: 6+ years of engineering experience with deep relational database depth. You've designed production schemas from scratch, written non-trivial server-side logic, and shipped data-heavy features. You speak fluently about indexes, constraints, migrations, schema evolution, and the architectural trade-offs among different relational models. High proficiency with PostgreSQL is strongly preferred. Multi-Tenant SaaS Architecture Expertise. Proven experience designing schemas, data isolation layers, and access patterns for systems serving multiple distinct enterprise clients or state agencies. Shipped LLM features in production. You've built and maintained a user-facing feature that uses LLM APIs (Anthropic, OpenAI, Gemini, or similar) and have opinions on structured output, eval design, prompt iteration, latency/cost tradeoffs, and where AI helps vs. hurts. Strongly preferred Client Services & Tech Delivery Comfort . Experience working in product-as-a-service, government tech, or professional services engineering for external clients. You understand that success means delivering robust software that balances the ultimate goal of best serving end users with the need to satisfy complex external compliance and client requirements. Polyglot Fluency (Python, JS/TS, SvelteKit). Our stack today uses Python for data pipelines, JavaScript/TypeScript in our SvelteKit frontend, and Node sync scripts. SvelteKit experience is a bonus, but we prioritize engineers who can confidently adapt to new languages with minimal friction. Also valuable Experience with classification/categorization tasks at scale. Background in edtech, govtech, or public-interest technology . Familiarity with Airtable APIs, GitHub Actions , or other low-friction automation tooling. How you work We're a small product engineering team with real traction and a wide surface area. That shapes who thrives here: You're energized by ambiguity and don't need a perfectly defined ticket to make progress. You enjoy structuring real-world complexity. You don’t expect pristine upstream data, and are energized by the challenge of designing highly structured, elegant internal systems that seamlessly ingest and standardize unpredictable data from external partners. You communicate technical trade-offs exceptionally well. You can confidently evaluate system feasibility, surface the right architectural questions, and push back constructively when you think a product decision compromises data integrity. You're excited to pair closely with another senior engineer . You’ll share ownership, code reviews, and design decisions. You develop thoughtfully with AI . You use tools like Claude Code for speed where they excel, and know exactly when to step in yourself. You care about building tools that serve families. You care about making a real impact on K–12 education, and you're up for the pragmatism that comes with shipping production software to state agencies and tens of thousands of users. How we work together: We ship good enough over perfect — but we care about doing it right, not just fast. That balance is something we actively talk about and recalibrate continuously. We keep things playful. The work matters, and the families we serve matter, but the team takes itself less seriously than the work. Async-first, with meaningful live connection time. Slack for day-to-day comms, Linear for issue tracking — and we make space for the fun stuff and the hard stuff live. We value transparency. No black boxes here — we actively bring the full team's perspectives into big decisions, and we give and ask for feedback often. Stack Frontend: SvelteKit (migration from vanilla JS underway), planned design system work Backend / Data: Python ETL pipelines, Node.js sync scripts, Airtable as a current data layer, migrating toward Postgres/Supabase AI: TBD API (Anthropic, Gemini, OpenAI) for production features (in active development) Infrastructure: GitHub Actions for CI/CD and pipeline orchestration, Vercel for new product deployments Tooling: Linear, GitHub, Slack, Claude / Claude Code How to apply Applications go through a short form . We’ll ask for: A resume or LinkedIn — whichever you keep current. A short note (a paragraph or two is fine) telling us about one production LLM feature you've shipped — what it did, what was tricky, what you'd do differently. A few sentences on a data architecture decision you made that you’re proud of that shows off your design thinking skills in complex PostgreSQL schema or multi-tenant architecture design. Optional: a link to a project, repo, or piece of writing that shows how you think. We'll get back to every applicant within two weeks. The process from there is a 30-minute intro call, a 45-minute technical conversation, a paid technical exercise (small, scoped, real), and a final round with the team. We particularly encourage applications from candidates whose backgrounds are underrepresented in tech.