JobsChicago Trading Company

AI Engineer

Chicago Trading Company · Chicago, IL · CTC Trading Group, LLC

Posted Sep 11, 2026 · We last checked this listing on Sep 20, 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.

Behavioral

Tell me about a project where you went from a vague idea to something running in production. What did the ambiguous part look like, and how did you resolve it?

ability to self-direct through undefined problems without needing a spec handed to them

What have you built with this technology on your own time, outside of work?

genuine personal engagement with the field versus resume-driven interest

Tell me about a time a tool or workflow you built for other engineers got pushback, or wasn't adopted the way you expected. What did you do?

how they handle building for internal users and whether they iterate based on feedback

Describe a case where you had to choose between a quick fix and building the underlying infrastructure properly. How did you decide?

judgment about when to invest in common infrastructure versus ship fast, relevant to their stated dual focus

Technical

Walk me through an agent or LLM-based tool you built end to end. What did the system look like, and what was the hardest part to get right?

whether they've actually shipped agent tooling versus just called an API once

Tell me about a time you had to design context or tool access for an agent so it didn't do something it shouldn't. How did you think about access controls or guardrails?

awareness of security and access control concerns in agent infrastructure, not just capability

How would you approach tracing and debugging an agent pipeline when something goes wrong three steps into a multi-step task?

depth of hands-on experience with observability in agentic systems versus theoretical familiarity

If inference latency became a bottleneck for a shared internal service, what levers would you look at first?

real understanding of inference infrastructure and performance tradeoffs, not just model-layer knowledge

How comfortable are you moving between Python, C++, and Java on the same project, and can you give an example where that mix actually mattered?

verifying claimed language breadth is real rather than a checkbox

How do you think about evaluating whether a model or agent is actually good at a task, especially before it has a track record in production?

depth on evaluation and benchmarking methodology, called out as a nice-to-have but core to reliability

Situational

Say you're bringing a new coding agent or harness into the firm. How would you evaluate whether it's actually better than what engineers already use?

judgment on model/harness tradeoffs and whether they'd rely on hype versus real benchmarking

You're building a tool for traders, not engineers. How does your approach to the interface or the workflow change compared to building something for other developers?

whether they can adapt technical work to different user sophistication and actually talk to non-engineers

Suppose a quant asks you to prototype an agent for backtesting or simulation work. What questions would you ask before writing any code?

whether they'd dig into the actual workflow and constraints before building, given no finance background is assumed

Practice this interview out loud.

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The full job description

As published by Chicago Trading Company.

<div class="content-intro"><p>Chicago Trading Company (CTC) is a premier proprietary trading firm specializing in options market making. &nbsp;Our collaborative culture fuels innovation in quantitative research, systematic trading strategies, and cutting-edge trading technology. &nbsp;For over three decades CTC has provided critical liquidity across derivatives exchanges worldwide - making them fairer, more transparent, and more efficient.</p> <p>We strive to be the most innovative firm in the industry today, tomorrow, and long into the future while upholding ethical excellence. We believe that CTC makes a positive impact on the markets, the lives of our employees, and all the communities to which we belong. Started in 1995 by a team of forward-thinking Traders, we are proud to call ourselves an industry leader that keeps making markets and each other better.</p></div><p><strong>WHAT YOU'LL DO</strong></p> <ul> <li>Build agent tooling used by CTC's engineers, quants, and traders.</li> <li>Bring new models, coding agents, and agent harnesses into CTC as the ecosystem evolves.</li> <li>Build the common infrastructure needed to support them, including inference, configuration, integrations, tracing, and access controls.</li> <li>Build AI tools and interfaces for specific roles and workflows across the firm.</li> <li>Improve the performance and reliability of the systems we run, from shared services to model inference.</li> <li>Prototype new uses for agents in areas like research, simulation, and trading.</li> <li>Work directly with users to understand their workflows and guide what we build next.</li> </ul> <p><strong>WHAT WE'RE LOOKING FOR</strong></p> <ul> <li>Experience building software with LLMs and agents, including tools, context, orchestration, and model APIs.</li> <li>Familiarity with coding agents and the tradeoffs between different models, providers, and harnesses.</li> <li>Comfortable working in Python, C++, and/or Java.</li> <li>Experience building software used by other engineers or end users.</li> <li>Comfortable working across application code, developer tooling, infrastructure, and user-facing software.</li> <li>Demonstrated ability to take ambiguous problems from idea through production.</li> <li>Hands-on use of this technology outside of work, including projects or experiments you've built for yourself.</li> </ul> <p><strong>NICE TO HAVE</strong></p> <ul> <li>Experience with model evaluation or benchmarking.</li> <li>Experience with inference optimization, fine-tuning, or post-training.</li> <li>Experience in financial markets or trading environments.</li> <li>Experience with quantitative research, market data, simulation, or backtesting.</li> </ul> <p><span style="color: rgb(255, 255, 255);">&nbsp;this job entirely</span></p><div class="content-pay-transparency"><div class="pay-input"><div class="description"><p><strong>Compensation</strong></p> <p>The salary range for this role is listed below. This role is also eligible for an annual discretionary bonus. The discretionary bonus will be dependent upon the individual’s skills, experience, qualifications, and firm performance.&nbsp;</p></div><div class="title">Salary Range</div><div class="pay-range"><span>$175,000</span><span class="divider">&mdash;</span><span>$225,000 USD</span></div></div></div><div class="content-conclusion"><p>Most teams at CTC, with the exception of Trading, follow a hybrid workplace model, subject to change based on business need.</p> <p><strong>Our Benefits&nbsp;</strong></p> <p>We strongly believe in the well-being of our employees and their families so we offer outstanding benefits to support you both professionally and personally. These benefits include generous time off, insurance coverage, paid parental leave, free breakfast and lunch (plus healthy snacks, of course), wellness reimbursement, and a variety of other benefits focused on providing the best employee experience.&nbsp;</p> <p><em>(Disclaimer: interns and contractors are not eligible for benefits at CTC)&nbsp;</em></p> <p><strong>Our Commitment to Diversity, Equity and Inclusion</strong></p> <p>At CTC, we aim to cultivate a workplace that celebrates diversity and each person feels included, engaged and empowered. Where each of us feels we belong. We are committed to having a diverse workforce and are proud to be an equal opportunity employer. CTC does not discriminate on the basis of race, religion, color, national origin, sex, gender, gender expression, sexual orientation, age, marital status, veteran status, or disability status. We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, to perform crucial job functions, and to receive other benefits and privileges of employment.&nbsp;</p> <p>If you have a disability and believe you need a reasonable accommodation in order to search for a job opening or to apply for a position, please contact us at info@chicagotrading.com. Note that emails sent to this email account for non-disability related issues, such as following up on an application, will not receive a response.</p> <p><strong>Use of Artificial Intelligence (AI)</strong></p> <p>Information submitted by job applicants may be subject to review and analysis by automated systems, including Artificial Intelligence (AI), as part of the recruitment process. Such systems are utilized to enhance the efficiency and effectiveness of our hiring procedures. Applicants are advised that any information provided may be evaluated by AI tools to ensure an equitable and thorough assessment.</p></div>

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