Principal Engineer
About the role
Principal-level engineering role at Vouch focused on building and governing a platform for agent-built software, advancing bounded contexts in the backend, and delivering production AI-driven insurance work. Reports directly to the CTO in a hybrid Chicago-based environment.
Responsibilities
- Own the platform that governs agent-built software. Build and operate a governance harness with markdown specifications, traceability, deterministic gates, tamper-evident evidence, and LLM-review workflows.
- Make bounded contexts real across our backend with enforced architecture, context maps, anti-corruption layers, and CI boundary checks.
- Ship agentic systems that perform real insurance work with multi-week agent workflows, tool contracts, and capability boundaries.
- Make model behavior measurable with eval suites, golden datasets, LLM tracing, and observability of cost and provenance; manage autonomy through evidence.
- Run platform and delivery engineering at scale (AWS multi-account estate in Terraform, GitOps, CI/CD pipelines generated rather than handwritten, ephemeral PR environments).
- Be the CTO’s architecture thought partner, contributing ADRs, design docs, and rigorous boundary discussions.
Qualifications
- A principal engineer with experience in AI, DevOps, and software architecture.
- Shipped domain-driven design with bounded-context maps and anti-corruption layers.
- Proficiency in multiple language ecosystems (Rust, TypeScript, etc.).
- Experience building and operating agent systems with evaluation gates, provenance capture, and autonomy control.
- Hands-on experience with infra at scale (infrastructure-as-code, GitOps, Kubernetes or similar).
- Strong written communication (design docs, ADRs, etc.) and ability to work in early-stage startup/high-growth contexts.
Skills
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 Lunch & Learns
- Wellbeing perks (Peloton, Fetch, OneMedical, Headspace care+, etc.)
- Caregiver support (dependent care FSA and Care.com membership)
- Regular performance reviews with goal setting and promotion opportunities
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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