Senior Software Engineer

## About the role As a Senior Software Engineer at OakPath, you'll build the product across the stack. You'll work directly with our CTO and a small founding team on everything from the conversational AI experience to the internal tools our navigators use every day. You'll ship code, talk to users (and navigators) about what's working, and have a real say in how the product evolves. This is a hands-on building role at an early-stage company. You'll write the code, review pull requests, instrument what you ship, and own features end-to-end. We're moving toward a July 2026 V1.0 launch in Sarasota, Florida, so the first few months will be heads-down execution with a clear target. After launch, you'll help shape what V2 looks like. You'll be comfortable with AI-native development. We use LLMs in the product and in how we build. You should have real experience designing prompts, evaluating model outputs, and integrating LLM APIs into production systems, not just experimenting on the side. ## Responsibilities - Build features end-to-end across our web platform: the chat experience users see, the navigator-facing case management tools, the resource matching engine, and the APIs that connect them. - Design and ship LLM-powered features that actually work in production: prompt design, structured outputs, evaluation harnesses, latency and cost tuning, fallbacks when models misbehave. - Help architect data models, infrastructure, and tooling that let us learn from every user interaction and improve the product week over week. - Review code, pair on hard problems, mentor more junior engineers when they join, and help establish engineering practices that scale past the first hires. - Collaborate with the CTO, navigators, CMO, and CEO to translate user needs into shippable software. Push back when scope is wrong. Suggest the simpler thing. - Watch user sessions, instrument what you build, and use that data to prioritize what to fix or improve next. - Share the on-call rotation once we're live. Things will break. You'll help fix them.