Senior AI Engineer

Company Description Deduction.com is a consumer fintech startup reimagining tax from a stressful, once-a-year “homework” exercise into a seamless, year-round financial partnership. We combine an agentic AI core with human CPA expertise to deliver highly accurate outcomes, a better customer experience, and fundamentally more efficient operations. We’re a small, high-ownership team. Engineers here don’t just implement—they define systems, make decisions, and own outcomes end-to-end. This is a remote-first role within the U.S., with optional in-person collaboration in New York and Chicago. Role Description We are looking for a Senior AI Engineer to join our growing AI team, working in lockstep with our Founding AI Engineer. While our founding team has laid the groundwork for our agentic core, your mission will be to expand, harden, and scale these systems. You’ll sit at the intersection of AI platform and production backend engineering. You aren't just building prototypes; you are building the durable infrastructure that allows our AI agent, Taylor, to reason through complex tax logic for our rapidly growing client base. This is a role for a builder who loves the challenge of making non-deterministic AI systems behave reliably in a highly regulated, high-stakes environment. What You'll Do Architect & Scale AI Systems : Work closely with the Founding AI Engineer to evolve our AI systems to a robust, governed, cutting-edge platform. Harden the Reasoning & Context Layer: Design sophisticated context engineering systems—managing memory and state while improving reliability, performance, and user experience. Build a Multi-Layered Evaluation Platform : Design and implement a robust system for continuous quality improvement, leveraging comprehensive offline test suites, LLM-as-a-judge scoring (AI Auditor), and production-based CPA moderation to create a data flywheel. Full-Stack AI Delivery : Write production-ready TypeScript (Node.js), ensuring AI features are seamlessly integrated into our core fintech platform. Security-First Design: Ensure context boundaries and data retrieval paths natively enforce strict security, privacy, and compliance guardrails to protect client data. Lead AI-Native Development : Set the standard for using AI to build AI—leveraging advanced coding assistants and automated testing to maintain high velocity and socializing best practices across the team. Core Requirements Production AI Experience : You have a track record of taking AI features beyond "demo-ware" and into production at scale. Context Engineering & AI Orchestration Mastery : Proven experience building systems where the primary challenge is managing context, memory, state at scale. Collaborative Architect : You enjoy working closely with other senior leads to brainstorm, peer-review, and iterate on complex system designs. The Stack: TypeScript (Node.js). Production experience with AI orchestration and evaluation. Familiarity with observability tooling is a plus. Fintech/Regulated Context : You understand that in tax, "mostly right" is wrong. You have the discipline required for building in a regulated space. Growth Mindset : You are ready to go from zero → one → scale with minimal friction, leaning into the evolving nature of the AI stack. Early-Stage Appetite: You thrive in environments where priorities shift fast, scope isn't always locked. You'd rather ship, experiment, and iterate than wait for a perfect spec. AI-Native Development You actively use AI tools as a core part of your development workflow (not optional) You believe the software engineer’s job is fundamentally changing—and you lean into that shift