New opportunity

AI Engineer

Vouch, Inc · Chicago, United States

About this role

Vouch is building AI software to support judgment-heavy insurance work in a regulated domain. The AI Engineer will help develop an LLM-based system that learns from experts, operates under human judgment, and improves measurably while remaining durable and auditable. The role is based in Chicago, IL, with hybrid flexibility; team members must work in the office at least Tuesday, Wednesday, and Thursday.

Responsibilities

  • Ship agentic insurance workflows end to end, defining tool contracts, capability boundaries and approval gates, then owning changes through review, deployment and production.
  • Extend a durable-execution system with pinned worker versioning and a CI replay-compatibility gate so interrupted workers can resume without losing state.
  • Maintain deterministic corpus tests used as merge gates, diagnostic evaluation suites, characterization corpora, LLM tracing, and token and cost observability. Version, snapshot-test and review prompts and tool definitions as code.
  • Develop the event and data infrastructure connecting agents to systems of record, including schema-governed events, object storage, and OLTP and OLAP databases. Use coding agents in development, write design documents, review for silent failures, and resolve production issues.

Required background:

  • Hands-on experience with LLM agent systems used by real users, including tool-calling patterns, MCP, the Anthropic SDK or equivalents; fluency in a strictly typed codebase; and production-service fundamentals such as API design, data contracts, authorization boundaries and observability.
  • Ability to implement safety properties in code, test model capabilities with evaluations, communicate tradeoffs clearly in writing, and deliver reliable, traceable production changes. Prior experience in and passion for early-stage startups and/or high-growth environments.

Preferred background: Production durable-execution engines; event-driven systems with schema governance, pub/sub, a schema registry, Avro or Protobuf; LLM evaluation and observability; building and consuming MCP servers; data lake or warehouse-adjacent engineering; experience in regulated domains such as insurance, fintech or healthcare; and frontend development.

The posted pay range is 180,000–220,000 USD per year for Chicago. Vouch also lists equity, health, dental and vision insurance, parental leave, flexible vacation, wellness and technology allowances, professional development, and caregiver support.

For full details about this role, click “Apply on company site” to view the employer’s original posting.

Skills for this role

AI agentsLarge language modelsAgentic workflowsTool callingMCPAnthropic SDKAPI designData contractsAuthorizationObservabilityDurable executionEvent-driven systemsPub/subSchema governanceAvroProtocol BuffersLLM evaluationLLM tracingPrompt engineeringObject storageOLTP databasesOLAP databasesData engineeringStrictly typed programmingFrontend developmentTechnical writing

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Get interview-ready for this role

A focused preparation guide, built around this job’s responsibilities and requirements.

✦ AI-generated guide
Preparation suggestions, not the employer’s actual interview questions. Always check the original posting for current requirements.
01

Understand the role

What matters most

  • Ship governed agent workflows

    The role owns insurance workflows from tool contracts and capability boundaries through approval gates, review, deployment, and production. Prepare to explain how human judgment remains in control and how authorization and safety properties are enforced in code.

  • Preserve workflow state across failures

    Vouch uses pinned worker versions and a CI replay-compatibility gate so crashed workers can resume mid-workflow. Prepare to discuss durable execution, state recovery, and how changes are checked against in-flight work.

  • Make model behavior testable

    Deterministic corpus tests gate merges; evaluation suites diagnose behavior; characterization corpora protect refactors. Prompts and tool definitions are versioned and snapshot-tested, with tracing and token/cost observability.

  • Connect agents to systems of record

    The engineer runs two-way plumbing involving schema-governed domain events, object storage, and OLTP/OLAP databases. Prepare to discuss data contracts and how agent actions remain traceable to authoritative records.

  • Own traceable production changes

    The posting emphasizes small increments, design documents, substantive review for silent failures, and fixing production issues. Written tradeoffs and follow-through matter alongside implementation.

Likely challenges to think through

  • Balance experimentation with consequential decisions

    Likely preparation hypothesis: rapid LLM prototyping may conflict with the controls needed for judgment-heavy insurance work. Prepare an example of testing a proposed capability with evaluations while keeping approvals and authorization outside the model's discretion.

  • Evolve code without breaking in-flight workflows

    Likely preparation hypothesis: changing workers, tools, or event schemas could threaten replay or downstream compatibility. Prepare to reason through versioning, compatibility tests, and recovery after an interruption.

  • Detect failures that passing tests miss

    Likely preparation hypothesis: deterministic merge gates cannot cover every model behavior or delayed downstream error. Prepare to explain how characterization tests, tracing, and review could expose misleading outputs or silent data failures before and after release.

03

Practice your answers

Technical practice

How would you design an agentic insurance workflow that stays under human judgment?

What to coverThe role calls for tool contracts, capability boundaries, approval gates, and ownership through production. Suggested answer focus: define what the agent may do, what requires human approval, and how those boundaries are enforced and tested.

Which safety properties belong in code rather than prompts?

What to coverThe posting explicitly asks engineers to implement safety properties in code and understand authorization boundaries. Suggested answer focus: contrast enforceable checks with model instructions, including how to prevent an unauthorized tool action.

How would you make an interrupted workflow resume without losing state?

What to coverThe described system uses pinned worker versioning and a replay-compatibility gate in CI. Suggested answer focus: explain state persistence, compatible replay after a code change, and tests for a crash mid-workflow.

How would you distinguish merge-gate tests from diagnostic model evaluations?

What to coverThe posting distinguishes deterministic corpus tests, diagnostic eval suites, and characterization corpora used before refactors. Suggested answer focus: explain what each detects and how you would investigate a behavioral change rather than relying on a single score.

How would you manage changes to prompts and tool definitions?

What to coverVouch describes these as versioned, cache-stable, snapshot-tested artifacts reviewed like code. Suggested answer focus: discuss change review, regression detection, and the trade-off between stable behavior and improving a prompt or tool contract.

How would you evolve a schema-governed domain event?

What to coverThe role involves an event bus and schema-governed events; schema registries and Avro or Protobuf are listed as nice-to-haves. Suggested answer focus: cover producer-consumer compatibility, validation, and what happens when an event cannot be processed.

How should an agent exchange data with systems of record?

What to coverThe posting names two-way plumbing, object storage, and OLTP and OLAP databases. Suggested answer focus: distinguish operational writes from analytical use, and explain how data contracts protect the systems of record.

How would you diagnose a production agent run with unexpected cost or behavior?

What to coverThe role maintains LLM tracing and token/cost observability and owns production issues. Suggested answer focus: describe the trace and cost signals you would inspect, how you would isolate a failure, and how you would verify a fix.

How would you implement a typed tool-calling integration for real users?

What to coverThe posting asks for experience with tool-calling patterns, MCP, the Anthropic SDK or equivalents, and a strictly typed codebase. Suggested answer focus: explain typed inputs and outputs, error handling, and validation at the tool boundary without assuming a particular SDK is required.

What silent failure would you look for in a review of an agent workflow?

What to coverThe posting emphasizes catching failures such as an empty string that causes trouble several stages later. Suggested answer focus: trace an invalid value across stages and describe the validation, tests, and observability that would expose it early.

Behavioural practice

Tell me about a time you changed a technical decision through a design document or review.

What to coverThe team describes design docs, review threads, and written trade-offs as central to its work. Suggested practice: use situation, action, and result to show how you made the reasoning clear and responded to disagreement.

Tell me about a production issue you owned through a correctness fix.

What to coverThe posting expects production ownership and treats correctness rework as part of finishing the job. Suggested practice: describe the situation, your diagnosis and actions, and the verified result without overstating certainty.

Tell me about a promising prototype you evaluated and then revised or removed.

What to coverThe role values testing model capabilities with evals and deleting approaches that do not survive real use. Suggested practice: give the situation, the evidence that changed your view, your action, and the result.

Tell me about using a coding agent while remaining accountable for the output.

What to coverThe posting says the team uses coding agents in daily development and reviews for silent failures. Suggested practice: explain the task, how you directed and checked the work, and what the result taught you.

Tell me about delivering in small increments amid changing requirements.

What to coverThe role is on a small team in an evolving codebase and emphasizes traceable, repeated delivery. Suggested practice: outline the situation, how you scoped and communicated each increment, and the result.

02

Sharpen your knowledge

Topics to prepare

  • Agent authority and human approval

    The role designs tool contracts, capability boundaries, and approval gates for insurance work under human judgment. Suggested revision exercise: diagram an agent action that reads a record, proposes a change, and waits for approval; mark where authorization and safety checks must be enforced in code rather than prompts.

  • Durable execution and replay compatibility

    The posting describes pinned worker versioning and a CI replay-compatibility gate so crashed workers can resume without losing state. Suggested revision exercise: trace a workflow through a crash and a worker update, then identify which state and versioning assumptions make replay safe.

  • Evidence for model behavior

    Deterministic corpus tests gate merges, while evaluation suites diagnose behavior and characterization corpora pin behavior before refactors. Suggested revision exercise: classify example failures by which test or evaluation would detect them, and explain what each result would and would not establish.

  • Event and data boundaries

    The role connects agents to systems of record through schema-governed domain events, object storage, and OLTP/OLAP databases. Suggested revision exercise: sketch how an approved agent action becomes a domain event and reaches a system of record; identify schema and authorization boundaries.

  • Production reliability and written reasoning

    The posting emphasizes API design, data contracts, observability, traceable changes, design documents, and reviews that catch silent failures. Suggested revision exercise: outline the tradeoffs in a small API change and list failure cases, including a valid-looking empty value that causes a later-stage error.

Skills to revise

  • Implement a bounded tool call

    Hands-on LLM agent experience and fluency in a strictly typed codebase are stated requirements; MCP, the Anthropic SDK, or equivalents are named examples. Suggested practice: implement a typed tool contract for a hypothetical insurance-record lookup, with input validation, an authorization check, and a human-approval gate before any write.

  • Test workflow recovery

    The role extends a durable-execution system with pinned worker versions and a replay-compatibility gate. Suggested practice: write a small workflow test that interrupts execution after a completed step, resumes it without repeating that step, and checks replay after a code change.

  • Build a model-behavior regression check

    The posting calls for deterministic corpus tests, diagnostic evaluations, characterization corpora, and versioned, snapshot-tested prompts and tool definitions. Suggested practice: create a small fixed set of tool-call cases, record expected outcomes, and review a prompt or tool-definition change against those outcomes.

  • Trace an agent action end to end

    LLM tracing and token/cost observability are part of the role. Suggested practice: instrument a sample agent request so its tool calls, approval decision, outcome, and token/cost totals can be inspected together; check whether a silent failure would be visible.

  • Review a schema-governed event change

    The role works with schema-governed events and data stores; schema registries and Avro/Protobuf are listed as nice-to-haves. Suggested practice: draft a domain-event schema change, examine how existing consumers would handle it, and write a short review note covering compatibility, data contracts, and failure paths.

04

Your preparation checklist

  • Build a role-evidence map

    Prepare a one-page map of the posting’s table-stakes—real-user LLM agents, strictly typed code, production-service fundamentals, safety in code, written tradeoffs, and early-stage or high-growth work—to specific examples you can discuss. Mark any gaps rather than inventing examples.

  • Rehearse an end-to-end agent walkthrough

    Choose a real project, if available, and explain its tool calls, contracts, authorization boundaries, human approval points, deployment, and production ownership. Use a diagram to distinguish enforced safeguards from prompt instructions.

  • Sketch a durable-workflow design

    As a preparation exercise, draw how an interrupted worker could resume without losing state. Address pinned worker versions, replay compatibility in CI, and failure cases; label your design choices as proposals, not Vouch’s implementation.

  • Prepare an evaluation artifact

    Draft a sample test plan separating deterministic corpus merge gates from diagnostic evals and characterization tests. Show how you would version and snapshot-test prompts and tool definitions, and inspect traces and token costs.

  • Diagram the system-of-record boundary

    Sketch a proposed flow between an agent, schema-governed events, object storage, and OLTP/OLAP data. Annotate data contracts, access checks, and where a silent failure might be detected.

  • Practice a written technical review

    Write a short design note or review comment that identifies a subtle failure path, weighs alternatives, and proposes a test or code-level safeguard. Be ready to explain how you verify coding-agent output and handle a production correction.

  • Bring focused questions for Vouch

    Prepare questions about how experts approve agent actions, how replay and corpus gates shape releases, and how engineers investigate failures. The page describes a case study or technical screen and hybrid attendance Tuesday through Thursday; confirm relevant logistics with the team.

AI-generated from the job information · Prepared Sep 30, 2026 (UTC)Useful preparation, not a guarantee of eligibility or an offer.

Availability last checked: Nov 4, 2026. Status can change after a check; confirm on the employer’s website. Report an issue · Our checking policy

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