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AI Engineer

Vouch
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Hybrid (Chicago, IL)$180k - $220kFull-timePosted 2mo ago

About the role

AI Engineer at Vouch (Chicago, IL) focused on building AI-powered insurance workflows, durable execution backbones, and measurable model behavior in a regulated domain. Hybrid role with in-office requirement (3 days/week in Chicago).

Responsibilities

  • 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. Extend substrate with pinned worker versioning and replay-compatibility gates in CI; ensure a crashed worker resumes mid-workflow without losing state.
  • Make model behavior measurable. Maintain deterministic corpus tests, eval suites, diagnostics, and LLM tracing/cost observability.
  • Treat prompts and tool definitions as engineered artifacts — versioned, cache-stable, snapshot-tested, and reviewed like code.
  • Run the event and data substrate. Manage event bus with domain events, object storage, databases, and integration between agents and systems of record.
  • Work with AI, on AI. Build with frontier coding agents and ensure trustworthiness of AI coworkers.
  • Review with teeth. Identify silent failure paths before production.

Qualifications

  • Production service fundamentals: API design, data contracts, authorization boundaries, observability.
  • Hands-on experience with LLM agent systems — tool-calling patterns, MCP, the Anthropic SDK, or equivalents — running in front of real users.
  • Fluency in a strictly-typed codebase.
  • You put safety properties in code, not in prompts — and you can say why.
  • Clear written communication about tradeoffs; decisions documented in design docs and threads.
  • Prior experience in and passion for early-stage startups and/or high-growth environments.

Skills

Required:AI-native problem solvingFrontier models and AI toolingLLM agent systems and toolingStrictly-typed codebase
Nice to have:Durable-execution and reliability

Benefits

  • Competitive compensation and equity packages
  • Health, dental, and vision insurance
  • Parental leave
  • Flexible vacation time
  • Wellness allowance
  • Technology allowance
  • Company-sponsored personal and professional development
  • L&D partnerships with Ethena and monthly Lunch & Learns
  • Wellbeing perks (Peloton, Fetch, OneMedical, Headspace care+ etc.)
  • Caregiver Support: seed into dependent care FSA and Care.com membership
  • Regular performance reviews with goal setting and development discussions
Last updated Oct 14, 2026. Interested? Apply on the company site.
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About Vouch

Insurance and risk management tools for startups and growth-stage…

Insurance... sounds slow, old-fashioned, and unexciting. Exactly. Insurance is broken, and it's failing fast-moving, innovative startups. Vouch is a new, technology-first insurance company backed with $185M in funding from world-class investors. Like Stripe for payments or Brex for credit cards, Vouch is creating the go-to business insurance for high-growth companies. We're doing this by making insurance fast, responsive, and focused on our high-growth and innovative customers. Instead of printed PDF applications and week-long waits, Vouch is building new technology to solve real problems, writing policies that actually cover relevant startup scenarios, and designing simple experiences in an otherwise frustrating industry.

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