Principal Engineer

Vouch Insurance•Chicago, IL

11d•$245,000 - $285,000

About The Position

Vouch's engineering organization is becoming agent-native, with a significant and growing portion of its production code written by AI coding agents within human-governed guardrails. This role focuses on the critical layer of deciding what to build, maintaining architectural coherence, and ensuring the correctness of shipped software, as writing code has become less of a challenge. This principal-level individual contributor role reports directly to the CTO and has a broad mandate covering the entire Vouch estate. This includes a harness for agent-built software (the first ownership deliverable), production AI for judgment-heavy insurance work, a backend requiring the realization of bounded contexts, and the underlying cloud platform. The company has extracted machinery that enabled a small team to ship approximately 1,100 governed changes in seven weeks with a sub-1% change-failure rate, and is now generalizing this into a platform. This role will be instrumental in answering the remaining technical questions.

Requirements

Principal engineer with expertise in AI engineering, DevOps, and software architecture.
Shipped domain-driven design, including enforcing bounded contexts, implementing anti-corruption layers, and performing hexagonal refactors, with an understanding of when patterns are overkill.
Proficiency in more than one language ecosystem (e.g., Rust, TypeScript) and understanding of their respective disciplinary demands.
Experience building and operating agent systems for real users, including tool contracts, capability boundaries, approval gates, and trustworthy machinery like eval gates and provenance capture.
Ability to test hypotheses about model capabilities with evals rather than shipping on hope.
Experience running infrastructure for others, including infrastructure-as-code at scale, GitOps, container orchestration, secrets management, and observability-as-code, with on-call experience.
Treating delivery machinery (CI/CD, environments, releases) as a product with users and arguing migrations based on cost and risk.
Ability to reason in writing through ADRs, design docs, and review comments.
Ability to multiply impact by enabling engineers and agents.
Experience in and passion for early-stage startups and/or high-growth environments.

Nice To Haves

TypeScript, Python, and/or Rust in production.
Shipped record of brownfield modernization (strangler migrations, context extraction, boundary enforcement in CI).
Durable-execution engines and event-driven systems with schema governance.
Experience with Eval frameworks, LLM observability, and MCP.
Background in insurance or other regulated categories.

Responsibilities

Own the platform that governs agent-built software, including a harness where markdown specifications compile to a traceability lock, deterministic gates for completion, tamper-evident evidence for every agent action, and a multi-vendor panel of LLM reviewers.
Transition the platform from a working extraction to an adopted system, defining its next milestone, building its plugin surface, operating and scoring review seats, and proving its generalization beyond its original repository.
Implement bounded contexts across the backend estate, transforming design-doc DDD into enforced architecture with context maps, anti-corruption layers, and CI-running boundary checks, without impeding daily team shipments.
Ship agentic systems for real insurance work, including durable multi-week agent workflows with human approval gates, tool contracts, capability boundaries, and planner/executor orchestration.
Make model behavior measurable and autonomy earned through eval suites as merge gates, golden datasets, LLM tracing, token/cost observability, and calibration of LLM reviewers against ground truth.
Run platform and delivery engineering at organization scale, managing an AWS multi-account estate in Terraform via GitOps, two orchestrators in production, generated CI/CD pipelines, and ephemeral environments per pull request.
Serve as the CTO's architecture thought partner and raise the engineering bar through strategic design sessions, impactful ADRs, insightful review comments, specifications for both humans and agents, mutation-testing bars, and adversarial review.

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: access to many wellbeing perks, including Peloton, Fetch, OneMedical, Headspace care+, etc.
Caregiver Support: company seed into the dependent care FSA and company sponsored Care.com membership.
Regular performance reviews: Vouch conducts regular performance discussions with all team members, offering goal setting and check-ins, development discussions, and promotion opportunities.