Jobs › Options Clearing Corporation

Associate Principal, Artificial Intelligence Engineering

Options Clearing Corporation · Chicago, IL · $127,900–$176,800 a year · Full time

Posted Sep 18, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about an AI system you shipped that behaved differently in production than in testing. What happened and what did you change?

What they are checking: Real production experience with nondeterministic systems and how they learn from surprises.

Tell me about a time you mentored a junior engineer through a hard technical problem.

What they are checking: Mentorship ability, which the posting names as part of the role.

What would you do

This is a largely greenfield environment. How would you decide which infrastructure to build now versus later?

What they are checking: Pragmatism in a new team, avoiding both overbuilding and shortcuts that later block compliance.

A business stakeholder wants an agent to make decisions that you think need a human in the loop. How do you handle it?

What they are checking: Willingness to push back on risky automation and explain the tradeoff in business terms.

How would you explain to model risk or compliance teams how your agent reaches its answers?

What they are checking: Ability to make AI systems auditable and understandable for oversight functions in a regulated firm.

About the work

Walk me through how you would design an agentic system on Claude and AWS that answers questions over internal risk documents, from architecture to production.

What they are checking: End-to-end ownership of an agentic AI system, including retrieval, tools, orchestration and deployment.

How do you build an evaluation pipeline for an agent so you can tell whether a prompt or model change made it better or worse?

What they are checking: Rigor about evals, which is what separates reliable production agents from demos in a regulated firm.

In a regulated clearinghouse, what guardrails would you put around an agent that can call internal tools?

What they are checking: Judgment on permissions, human review, logging and failure modes when agents can take real actions.

How do you decide what context to give an agent and what to leave out?

What they are checking: Practical understanding of context engineering, cost and accuracy tradeoffs in agent design.

How would you monitor an agent in production to catch quality drift, cost spikes or misuse?

What they are checking: Operational maturity for AI systems, including observability beyond uptime.

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The full job description

As published by Options Clearing Corporation.

To be considered for this position, applications and resumes are accepted only through our careers site by directly applying to the posted job. We do not accept unsolicited resumes or sales solicitations from staffing agencies. Any OCC employee wishing to submit a referral must do so through their Workday account. Any resume submitted outside of an active job posting will not be considered for employment. Summary OCC's AI Research & Engineering (AIRE) team is building the company's first generation of agentic AI capabilities on Anthropic's Claude models and AWS infrastructure. The Associate Principal, AI Engineering owns the design and delivery of agentic AI systems end-to-end, mentors junior engineers, and contributes technical judgment on AI application and/or AI infrastructure work in a largely greenfield environment. Primary Duties and Responsibilities: To perform this job successfully, an individual must be able to perform each primary duty satisfactorily. • Own the design and delivery of agentic AI systems end-to-end, from architecture through production deployment • Architect agent orchestration patterns, tool and context integration, and evaluation pipelines for reliability in a regulated environment • Own AI infrastructure supporting AIRE's agents and applications on AWS, and contribute to the team's growing infrastructure self-sufficiency • Implement technical safeguards against AI-specific risks, including hallucination detection, prompt injection defense, and output validation, in collaboration with OCC's AI Governance function • Build audit logging and human-in-the-loop checkpoints into agentic workflows so agent actions remain traceable and reviewable in a regulated environment • Mentor Associate and Senior Associate engineers through code and architecture review • Contribute technical point of view to the team's evolving engineering standards and practices, in partnership with the Executive Director Supervisory Responsibilities: None (no direct reports; mentors junior engineers without formal supervisory authority) Qualifications: The requirements listed are representative of the knowledge, skill, and/or ability required. Reasonable accommodations may be made to enable individuals with disabilities to perform the primary functions. • Experience mentoring or elevating the work of junior engineers • Demonstrated ownership of production systems from design through deployment • Ability to work effectively in a still-forming, fast-moving team environment • This position is not eligible for employment visa sponsorship. Candidates must be legally authorized to work in the United States without the need for sponsorship now or in the future. Technical Skills: • Required: Strong Python; proficient SQL; solid distributed systems and API design fundamentals • Required: Hands-on experience building LLM-powered applications or agentic systems • Required: Working knowledge of AI-specific risk areas (prompt injection, output validation, hallucination mitigation, data privacy), or demonstrated ability to build this expertise quickly • Required: Cloud infrastructure experience (AWS preferred); comfort with Docker, CI/CD, and containerization fundamentals • Preferred: Direct experience with Claude, the Anthropic API, or Claude.ai/Console • Preferred: Experience designing agent orchestration or Model Context Protocol (MCP)-based integrations • Preferred: Production experience operating LLM-powered applications or agentic systems at scale • Preferred: Kubernetes and infrastructure-as-code (Terraform) • Preferred: Background in financial services, derivatives, or other regulated industries • Preferred: Exposure to AI security practices such as red-teaming or adversarial testing of model inputs and outputs • Preferred: Data engineering experience (pipelines, data modeling), particularly for candidates interested in AI infrastructure work Education and/or Experience: • Bachelor's degree in Computer Science, Engineering, or a related technical field; Master's preferred • 4-7 years of software engineering experience, with production AI/LLM systems experience preferred Certificates or Licenses: None required About Us The Options Clearing Corporation (OCC) is the world's largest equity derivatives clearing organization. Founded in 1973, OCC is dedicated to promoting stability and market integrity by delivering clearing and settlement services for options, futures and securities lending transactions. As a Systemically Important Financial Market Utility (SIFMU), OCC operates under the jurisdiction of the U.S. Securities and Exchange Commission (SEC), the U.S. Commodity Futures Trading Commission (CFTC), and the Board of Governors of the Federal Reserve System. OCC has more than 100 clearing members and provides central counterparty (CCP) clearing and settlement services to 19 exchanges and trading platforms. More information about OCC is available at www.theocc.com. Benefits A highly collaborative and supportive environment developed to encourage work-life balance and employee wellness. Some of these components include: • A hybrid work environment, up to 2 days per week of remote work • Tuition Reimbursement to support your continued education • Student Loan Repayment Assistance • Technology Stipend allowing you to use the device of your choice to connect to our network while working remotely • Generous PTO and Parental leave • 401k Employer Match • Competitive health benefits including medical, dental and vision Visit https://www.theocc.com/careers/thriving-together for more information. Compensation • The salary range listed for any given position is exclusive of fringe benefits and potential bonuses. If hired at OCC, your final base salary compensation will be determined by factors such as skills, experience and/or education. • In addition, we believe in the importance of pay equity and consider internal equity of our current team members as part of any final offer. • We typically do not hire at the maximum of the range in order to allow for future and continued salary growth. We also offer a substantial benefits package as noted on www.theocc.com/careers • All employees may be eligible for a discretionary bonus. Discretionary bonuses are based on various factors, including, but not limited to, company and individual performance and are not guaranteed. Salary Range $127,900.00 - $176,800.00 Incentive Range 8% to 15% This position is eligible for an annual discretionary incentive compensation award, for which the target range is listed above (see Incentive Range ). The amount of such award, if any, will be based on various factors, including without limitation, both individual and company performance. Step 1 When you find a position you're interested in, click the 'Apply' button. Please complete the application and attach your resume. Step 2 You will receive an email notification to confirm that we've received your application. Step 3 If you are called in for an interview, a representative from OCC will contact you to set up a date, time, and location. For more information about OCC , please click here . OCC is an Equal Opportunity Employer

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