Senior Software Engineer, Data Architecture

Outschool.org builds family navigation tools that help parents access and pay for educational resources through state-contracted services. The Senior Software Engineer will lead PostgreSQL data architecture, backend integrations, AI-powered compliance tooling, and migration from Airtable to a production Postgres database while improving Python ETL pipelines.

Responsibilities:

• 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!

Requirements:

• 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
• 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
• 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
• High proficiency with PostgreSQL is 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
• 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