New opportunity

AI Engineer

Optiver · Chicago, United States

About this role

Optiver seeks an experienced AI Engineer for its Applied AI and Platform Engineering team in Chicago. The role owns the lifecycle of production AI systems, from identifying opportunities and turning ambiguous business problems into solutions through deployment, operation and continuous improvement. The systems should automate workflows, support decision-making and accelerate engineering across the firm.

Responsibilities

  • Build AI products using Python and modern AI frameworks, including agent platforms, AI assistants, code review harnesses, evaluation frameworks and agentic research pipelines. Integrate them with internal systems, data platforms and third-party AI services.
  • Evaluate foundation models, agent architectures and workflows against capability, reliability, latency, security, cost and business impact. Define success metrics, benchmarks and observability to assess quality, safety, performance and production readiness.
  • Design scalable, resilient distributed systems with attention to state management, authentication, fault tolerance and operational reliability. Prototype emerging tools and models against measurable criteria before production investment.
  • Work with trading, research and business teams to refine requirements and turn successful use cases into reusable platform capabilities. Deliver maintainable software with automated testing and code reviews; monitor and improve production quality, reliability, latency, cost, governance and user outcomes.

Requirements

  • Bachelor's degree in Computer Science, Artificial Intelligence or a related technical field, and at least 6 years of professional software engineering experience, including extensive production Python application development.
  • Strong grounding in software architecture, object-oriented design, design patterns, distributed systems and testing. Experience designing, deploying and operating production LLM applications, including model evaluation, prompt engineering, tool calling, context management, agent orchestration and common failure modes.
  • Experience building quantitative evaluation frameworks, integrating AI with external tools, APIs, Model Context Protocol (MCP) and modern AI application frameworks, and operating highly reliable systems. Sound judgment about when to use AI versus conventional automation, a product mindset, problem-solving ability and strong cross-functional communication are required.

Compensation and benefits: The stated base salary range is $200,000—$200,000 USD. The position is also eligible for a discretionary bonus and benefits including a 401(k) match of up to 50%, insurance and 25 days of paid vacation plus market holidays.

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

Skills for this role

PythonSoftware architectureObject-oriented designDesign patternsDistributed systemsAutomated testingLarge language modelsAgent orchestrationPrompt engineeringTool callingContext managementModel evaluationEvaluation frameworksBenchmarkingObservabilityModel Context Protocol (MCP)API integrationState managementAuthenticationFault toleranceAI safetyCode reviewProduct developmentCross-functional collaboration

Your skill match

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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

  • Own production AI end to end

    The role spans identifying opportunities, translating ambiguous problems into solutions, deployment, operation, and continuous improvement. Prepare to explain decisions across that lifecycle, including measurable business outcomes.

  • Make evidence-based AI choices

    Optiver calls for evaluating models, agents, and workflows against capability, reliability, latency, security, cost, and impact. Be ready to describe success metrics, quantitative benchmarks, and criteria for production readiness.

  • Engineer reliable integrated systems

    The work includes Python AI products connected to internal systems, data platforms, external tools, APIs, MCP, and third-party services. Emphasize architecture, authentication, state management, fault tolerance, testing, and observability.

  • Improve systems after launch

    The posting explicitly assigns ongoing monitoring and improvement of quality, safety, reliability, latency, cost efficiency, governance, and user outcomes. Prepare to discuss how production evidence would guide changes.

  • Turn user needs into reusable capabilities

    The engineer partners with trading, research, and business teams to refine requirements, challenge assumptions, iterate, and evolve successful use cases into platform capabilities. Focus on how to balance a specific user need with maintainable reuse.

Likely challenges to think through

  • Prototype speed versus production assurance

    A likely tension, not a stated employer problem, is validating emerging models quickly without treating a promising demo as production-ready. Prepare a staged approach with measurable gates for evaluation, security, testing, and operational reliability.

  • Agent flexibility versus predictable behavior

    Because the role requires judgment about AI versus deterministic automation, a likely difficulty is deciding when an agent’s capability justifies its failure modes, latency, and cost. Prepare to compare alternatives against the same task metrics and explain fallback choices.

  • Local usefulness versus platform reuse

    Partnering with distinct teams while building reusable capabilities may create a trade-off between tailored workflows and common infrastructure. Prepare to explain how user feedback could shape a narrow first solution without hard-coding it into a platform.

03

Practice your answers

Technical practice

When would you use an LLM instead of deterministic automation for a workflow?

What to coverThe posting calls for judgment about when AI is appropriate. Preparation suggestion: compare task variability, correctness requirements, measurable benefit, cost, and the option to keep critical steps deterministic.

How would you structure a maintainable Python AI product?

What to coverThe role emphasizes production Python, software architecture, object-oriented design, and reusable platform capabilities. Preparation suggestion: explain component boundaries, interface design, testing strategy, and how the design could accommodate changing models or integrations.

How would you manage prompts and context in a production LLM application?

What to coverThe posting names prompt engineering, context management, and common LLM failure modes. Preparation suggestion: discuss relevance and context limits, prompt iteration, and ways to detect unsupported or inconsistent outputs.

How would you design an agent that calls internal tools and external APIs?

What to coverThe role includes agent orchestration and integrations with tools, APIs, and Model Context Protocol (MCP). Preparation suggestion: cover tool selection, input validation, authentication, permission boundaries, and handling failed or repeated calls.

How would you evaluate an AI assistant before production release?

What to coverThe posting calls for quantitative evaluation frameworks, benchmarks, and production-readiness criteria. Preparation suggestion: define representative tasks, baseline comparisons, quality and safety metrics, and thresholds tied to the intended user outcome.

How would you choose between foundation models or agent workflows?

What to coverThe role explicitly weighs capability, reliability, latency, security, cost, and business impact. Preparation suggestion: describe a controlled comparison and explain which trade-offs would change your choice for a particular use case.

How would you make a distributed AI system resilient?

What to coverThe posting highlights scalability, state management, fault tolerance, and operational reliability. Preparation suggestion: explain where state lives, how failures are isolated or retried, and how you would preserve correctness during partial outages.

What would you monitor after deploying an AI system?

What to coverThe role includes operating systems and improving quality, reliability, latency, cost, governance, and user outcomes. Preparation suggestion: distinguish service-health signals from output-quality measures, then describe how observations would drive investigation and improvement.

How would you test and review AI-assisted software development?

What to coverThe posting requires automated testing, thoughtful code reviews, and reliable AI-assisted development. Preparation suggestion: cover functional tests, integration tests, review of generated changes, and checks against business requirements.

How would you validate an emerging AI tool before investing in production?

What to coverThe role calls for rapid prototypes assessed against measurable success criteria. Preparation suggestion: define a narrow use case and baseline, then explain what evidence on capability, risk, and operating cost would justify further investment.

Behavioural practice

Tell me about a time you turned an ambiguous user need into a technical solution.

What to coverThe role involves translating ambiguous business challenges into measurable outcomes. Preparation suggestion: use situation, action, and result to show how you clarified the need, chose a scope, and assessed the outcome.

Describe a time you challenged an assumption while working with another team.

What to coverThe posting emphasizes partnering with trading, research, business teams, and end users to refine requirements. Preparation suggestion: give the situation, your specific action, and the result, including how you handled disagreement constructively.

Tell me about a production reliability problem you helped resolve.

What to coverOperating and continuously improving reliable production systems is central to the role. Preparation suggestion: explain the situation, your diagnostic and corrective actions, and the result without overstating what you personally controlled.

Describe an experiment that changed your technical direction.

What to coverThe posting calls for prototyping emerging approaches against measurable criteria. Preparation suggestion: set out the situation, what you tested and learned, the decision you made, and its result.

Tell me about a time you made a one-off solution reusable.

What to coverThe role includes evolving successful use cases into platform capabilities. Preparation suggestion: describe the original situation, how you identified shared needs and changed the design, and the resulting adoption or maintainability impact.

02

Sharpen your knowledge

Topics to prepare

  • Production LLM application design

    The posting requires experience with prompt engineering, tool calling, context management, agent orchestration and common failure modes. Revision exercise: diagram an assistant workflow and explain where it could return an incorrect answer, misuse a tool or lose necessary context.

  • Model selection and production readiness

    The role compares models and workflows on capability, reliability, latency, security, cost and business impact. Revision exercise: define a small set of success metrics and explain how benchmark results would inform a model choice or block a release.

  • Resilient distributed AI systems

    The posting emphasizes scalability, state management, authentication, fault tolerance and operational reliability. Revision exercise: sketch a distributed AI service, then reason through a failed dependency, a repeated request and recovery of state.

  • Software architecture and maintainability

    The requirements name object-oriented design, design patterns, testing and scalable applications. Revision exercise: compare two ways to separate model access, tool integration and business logic; explain how each affects testing and future changes.

  • AI versus deterministic automation

    The posting explicitly calls for judgment about when AI is appropriate and for measurable business outcomes. Revision exercise: take an ambiguous workflow request and compare an AI approach with conventional automation, stating assumptions, risks and a success measure.

Skills to revise

  • Build a production-style Python component

    Extensive production Python experience is required. Suggested practice: implement a small, modular AI-workflow component with input validation, error handling and automated tests; review it for maintainability as well as correct output.

  • Integrate tools, APIs and MCP

    The posting explicitly mentions external tools, APIs and Model Context Protocol (MCP). Suggested practice: implement or outline a bounded tool call, including authentication, response validation and handling an unavailable service.

  • Create a quantitative evaluation harness

    The role builds evaluation frameworks and uses metrics to guide model selection and prompt iteration. Suggested practice: assemble representative test cases, score outputs against stated criteria and compare two prompt or workflow versions, including failure cases.

  • Instrument and troubleshoot an AI workflow

    The posting calls for observability and continuous improvement of production quality, reliability, latency and cost. Suggested practice: specify what to record for each workflow step, then use a hypothetical latency or quality regression to identify the next investigation.

  • Refine a cross-functional use case

    The role partners with trading, research and business teams to clarify needs and develop reusable capabilities. Suggested practice: turn a vague request into clarifying questions, functional requirements, a measurable outcome and a brief explanation of what could be reused.

04

Your preparation checklist

  • Organize evidence for the stated requirements

    Prepare a fact sheet covering your degree, software engineering experience, production Python work, distributed systems, testing, and production LLM applications. The posting specifies a related bachelor’s degree and 6+ years of professional software engineering experience; do not fill gaps with assumed experience.

  • Build a production AI project walkthrough

    Choose a real project, if available, and outline the problem, your decisions, Python implementation, integrations, deployment, and subsequent improvements. Distinguish what you personally built from the wider team’s work.

  • Practice framing an ambiguous use case

    Draft a short example of how you would clarify a request from a trading, research, or business user, define a measurable outcome, and decide whether AI or deterministic automation is the better fit. This is a preparation exercise, not a stated interview task.

  • Sketch a resilient AI system

    Practice a design exercise for an assistant or agent integrated with internal systems and external tools. Include state management, authentication, security, fault tolerance, scalability, and operational reliability, as emphasized in the posting.

  • Prepare a quantitative evaluation plan

    Create a sample scorecard comparing model or agent options on capability, reliability, latency, security, cost, and business impact. Specify benchmarks, failure cases, observability, and criteria for production readiness.

  • Show how you would operate and improve it

    Prepare a concise account of testing, code review, monitoring, incident response, and iteration for a production system. Connect proposed measures to the role’s focus on quality, safety, governance, cost, and user outcomes.

  • Select cross-functional collaboration examples

    Prepare specific examples, if you have them, of refining requirements with end users, challenging an assumption, and turning a successful solution into something reusable. State the outcome and any limits of the evidence.

  • Write questions for the team

    Ask how Optiver identifies promising AI use cases, measures production success, and decides when a prototype should become a reusable platform capability. These questions follow from the advertised responsibilities; the posting does not specify the team’s answers.

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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