Hiring: AI Engineer Company: Vouch Insurance Location: Chicago, IL Job Posted Time: 2026-09-12 10:21:46 Employment Type: Hybrid Target Skills & Keywords : API Design, Avro, Data Lake, Event-Driven, LLM, Protobuf, Pub/Sub About the job Required Skills: •Vouch is building AI software for judgment-heavy insurance work: a system that learns from experts and gets measurably better week over week. We are early — a small team, real experts, real production usage, real customers, and a lot of unanswered technical questions. •You would join early in the system's life, in a rapidly evolving codebase that already carries more test code than source code. That ratio is not an accident; it is our style. •Ship agentic workflows end to end. Design tool contracts, capability boundaries, and approval gates for an agent doing real insurance work under human judgment — then carry your change through review, deploy, and production ownership. •Build on a durable-execution backbone. Our workflows run with pinned worker versioning and a replay-compatibility gate in CI; a crashed worker has to resume mid-workflow without losing state. You'll extend that substrate and understand it deeply. •Make model behavior measurable. Deterministic corpus tests are the merge gate; eval suites are the diagnostics; characterization corpora pin behavior before refactors. You'll maintain and grow that machinery, along with LLM tracing and token/cost observability. •Treat prompts and tool definitions as engineered artifacts — versioned, cache-stable, snapshot-tested, and reviewed like code, because they are code. •Run the event and data substrate. Event bus with schema-governed domain events, object storage, OLTP/OLAP databases, and the two-way plumbing between an agent and the systems of record it must respect. •Interface directly with AI, on AI. This team builds with frontier coding agents as daily instruments, and our specs are written to be read by humans and coding agents alike. You'll do both: use the tools hard, and build the system that makes an AI coworker trustworthy. Qualifications: •This role is a blend of two traits that are critical for success. Our system has to be genuinely novel and boringly reliable at the same time, and an engineer with only one of those instincts pulls the pod off balance. •You Are AI-native And Inventive •Frontier models are instruments you play daily — in how you build (coding agents, multi-model workflows, letting an agent draft while you direct) and in what you build (planners, classifiers, tool-calling systems). •You come at problems with approaches nobody asked for, and you are willing to be wrong out loud in service of moving the work. •"The model can probably do this" is a hypothesis you test with an eval, not a hope you ship on vibes. •You prototype fast, generalize what survives contact with reality, and delete what doesn't. •You Are Steady In Delivery And Reasoning •You ship in small, traceable increments, week after week; teammates can find the ticket from your branch name and the reasoning in your design doc. •You write your thinking down — design docs before lynchpin systems, and review comments that catch what tests miss: the uncalibrated confidence score someone will read as a guarantee, the trust boundary conflated with a durability guarantee. •Production is yours. You fix the OOM at the right layer and treat a correctness rework as finishing the job, not a "fast follow". Compensation: •Flexible work environment (work from home / hybrid options) •💰 Competitive compensation and equity packages Interested candidates, please apply directly through the job posting on company's career page or try via AI auto apply on this platform. Don't miss this opportunity to join a forward-thinking team!