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This position has closed. Chicago Trading Company removed this listing from their careers page on Oct 6, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Senior Engineer - Compliance Technology

Chicago Trading Company · Chicago, IL · Technology

Posted Oct 1, 2026 · We last checked this listing on Oct 5, 2026

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 a time you worked with compliance or legal staff to turn a regulation into software requirements.

What they are checking: Whether they can translate regulatory language into precise logic and ask the right clarifying questions.

Tell me about a system you owned end to end. How did you keep it reliable?

What they are checking: Whether they take ownership of operations and monitoring, not just initial development.

What would you do

A regulatory report goes out with incorrect data. How do you respond?

What they are checking: Whether they act quickly with compliance to fix, document and prevent recurrence of reporting errors.

Traders complain that a compliance check is slowing them down. How do you handle it?

What they are checking: Whether they can find solutions that respect both trading performance and regulatory requirements.

About the work

How would you design a system that monitors sales and pricing requests in real time for compliance issues?

What they are checking: Whether they can design streaming systems that are fast, reliable and produce alerts compliance can act on.

What regulatory reports might an options market maker need to produce, and what makes them hard to get right?

What they are checking: Whether they understand reporting obligations like CAT and the data quality challenges behind them.

How do you build compliance systems that keep up as trading venues change their rules?

What they are checking: Whether they design flexible, configurable systems instead of hard-coding rules that break with each change.

How would you test a surveillance system to make sure it catches the issues it is supposed to catch?

What they are checking: Whether they think about false negatives and test with realistic scenarios, not only normal data.

How do you make sure your systems handle data across multiple jurisdictions correctly?

What they are checking: Whether they understand that different regulators need different data, formats and timing.

How do you manage operational risk in trading through software?

What they are checking: Whether they understand controls like limits, kill switches and checks that prevent costly trading errors.

Practice this interview out loud.

Offer builds a real interview for this exact role at Chicago Trading Company from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

Practice this out loud

The full job description

As published by Chicago Trading Company.

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. 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. We are seeking a proactive and detail-oriented Compliance Software Engineer to join our dynamic team. You will be responsible for developing, implementing, and maintaining innovative solutions that support our market participation and ensure effective management of trading operational risk. Your work will be integral in real-time monitoring of sales and pricing requests, compliance with trading venue regulations, and the generation of regulatory reports across multiple jurisdictions. What you’ll do <ul class="ak-ul" data-local-id="51eee989-7179-4824-8b70-08cef2d081c6" data-prosemirror-content-type="node" data-prosemirror-node-name="bulletList" data-prosemirror-node-block="true"> <li data-local-id="21f63be6-dd5a-47a2-9a93-5e40497717d2" data-prosemirror-content-type="node" data-prosemirror-node-name="listItem" data-prosemirror-node-block="true">Design, build, and continuously improve real-time, high-throughput systems that monitor orders and quotes across venues, process large data sets, and carry out market-making obligations. <li data-local-id="d05b9011-2696-4e3f-ae46-11f5fdd079d4" data-prosemirror-content-type="node" data-prosemirror-node-name="listItem" data-prosemirror-node-block="true">Automate end-to-end compliance: detect prohibited trading behaviors, generate/submit regulatory reports (SEC, FSA, FINRA, etc.), and adapt controls to evolving rules and guidelines. <li data-local-id="0723e3f2-1b41-4825-aad0-1ad6ef22091f" data-prosemirror-content-type="node" data-prosemirror-node-name="listItem" data-prosemirror-node-block="true">Quickly fix production issues to ensure uninterrupted market operations. <li data-local-id="5208fee4-5be1-43a6-8d26-20d8f26783e5" data-prosemirror-content-type="node" data-prosemirror-node-name="listItem" data-prosemirror-node-block="true">Document architectures, processes, and changes to support audits and regulatory reviews. <li data-local-id="c88807eb-019a-4f74-8e41-c143203104ed" data-prosemirror-content-type="node" data-prosemirror-node-name="listItem" data-prosemirror-node-block="true"> Lead projects across multi-disciplinary teams in Trading, Tech and Operations. Must have - <ul class="ak-ul" data-local-id="539ec479-aeb7-4a81-8a4f-7c9805c042ec" data-prosemirror-content-type="node" data-prosemirror-node-name="bulletList" data-prosemirror-node-block="true"> <li data-local-id="0d5122ba-d4bd-40a1-bef4-88eb59d2562f" data-prosemirror-content-type="node" data-prosemirror-node-name="listItem" data-prosemirror-node-block="true">At least 5 years experience with real-time, latency sensitive trading or financial-services systems in Java and Python. <li data-local-id="b68a4719-fcb0-411e-9741-3bfaa0494d8a" data-prosemirror-content-type="node" data-prosemirror-node-name="listItem" data-prosemirror-node-block="true">Experience designing and building scalable systems, high-performance data pipelines and market-monitoring tools. <li data-local-id="591e7baf-142b-4778-b5f5-7814889a1238" data-prosemirror-content-type="node" data-prosemirror-node-name="listItem" data-prosemirror-node-block="true">Strong grasp of market-making, trading operations, risk management, and the applicable regulatory landscape. <li data-local-id="3f6550a2-9293-4603-a2fc-2763da403f13" data-prosemirror-content-type="node" data-prosemirror-node-name="listItem" data-prosemirror-node-block="true">Shown analytical and problem-solving capabilities; comfortable balancing multiple priorities in a highly regulated, fast-paced environment. <li data-local-id="832966e2-8c5d-4d38-9664-f6c9bab216b6" data-prosemirror-content-type="node" data-prosemirror-node-name="listItem" data-prosemirror-node-block="true">E xperience providing mentorship and feedback through code review and evaluating design decisions. Nice to have - <ul class="ak-ul" data-local-id="d97679ad-35fd-4438-8737-2a869be806ad" data-prosemirror-content-type="node" data-prosemirror-node-name="bulletList" data-prosemirror-node-block="true"> <li data-local-id="906972d5-ece9-4c4d-bd54-427f9ceb97f2" data-prosemirror-content-type="node" data-prosemirror-node-name="listItem" data-prosemirror-node-block="true">Experience with compliance/surveillance platforms or financial-regulation frameworks. <li data-local-id="a31f4482-858f-4b0d-8226-6f51df437b4d" data-prosemirror-content-type="node" data-prosemirror-node-name="listItem" data-prosemirror-node-block="true">Knowledge of operational-risk management tools. <li data-local-id="a1115c2c-8000-43b5-893d-430e4866d45f" data-prosemirror-content-type="node" data-prosemirror-node-name="listItem" data-prosemirror-node-block="true">Familiarity with cloud-native architectures and big-data technologies. Most teams at CTC, with the exception of Trading, follow a hybrid workplace model, subject to change based on business need. Our Benefits&nbsp; 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; (Disclaimer: interns and contractors are not eligible for benefits at CTC)&nbsp; Our Commitment to Diversity, Equity and Inclusion 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; 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. Use of Artificial Intelligence (AI) 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.