Principal Engineer

Vouch•Chicago, IL

20h•Remote

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 more complex challenges that remain, such as deciding what to build, maintaining architectural coherence, and ensuring the correctness of shipped software. This is a principal-level individual contributor position reporting directly to the CTO, with a broad mandate covering the company's entire technical estate. Key responsibilities include owning the platform for agent-built software, overseeing production AI for insurance work, evolving the backend with bounded contexts, and managing the underlying cloud platform. The role involves taking a proven system for governed agent-built software and generalizing it into a platform, addressing open technical questions along the way.

Requirements

Principal-level individual contributor with expertise in AI engineering, DevOps, and software architecture.
Shipped domain-driven design, including bounded-context maps, anti-corruption layers, and hexagonal refactors, with an understanding of when patterns are appropriate.
Proficiency in multiple language ecosystems (e.g., Rust, TypeScript) and understanding of their respective demands.
Experience building and operating agent systems for real users, including tool contracts, capability boundaries, approval gates, and trustworthy machinery (eval gates, provenance capture).
Experience testing hypotheses about model capabilities with evals.
Experience running infrastructure at scale, including infrastructure-as-code, GitOps, container orchestration, secrets management, and observability-as-code.
Experience with pager duty and on-call responsibilities.
Treating delivery machinery (CI/CD, environments, releases) as a product.
Ability to argue for migrations based on cost and risk.
Strong written communication skills for ADRs, design docs, and review comments.
Ability to multiply impact by enabling engineers and agents around them.
Experience in 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).
Experience with 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 its traceability, deterministic gates, evidence capture, and LLM reviewer panel.
Transition the platform from a working extraction to an adopted system, defining its next milestones, building its plugin surface, operating review seats, and proving its generalization capabilities.
Implement bounded contexts across the backend estate, enforcing architectural principles like context maps, anti-corruption layers, and CI boundary checks without hindering daily releases.
Ship agentic systems for insurance work, featuring durable multi-week workflows, 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.
Run platform and delivery engineering at scale, managing an AWS multi-account estate in Terraform via GitOps, orchestrators, generated CI/CD pipelines, and ephemeral environments.
Serve as the CTO's architecture thought partner, contributing to strategic design, ADRs, review comments, and specifications for both humans and coding agents.
Raise the bar for architectural standards and decision-making.

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.