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Experienced Software Engineer - US

Chicago Trading Company · Chicago, IL · $145,000–$225,000 a year · Technology

Posted Sep 11, 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 a time you had to make a system faster with a tight deadline. What did you cut, and what did you refuse to cut?

What they are checking: judgment about tradeoffs under time pressure and whether corners cut were the right ones

Describe the most complex distributed system you've worked on. What broke, and how did you find out it was broken before someone else told you?

What they are checking: experience with distributed systems at scale and whether they build or rely on proper monitoring

Tell me about a time your priorities changed suddenly, maybe mid-project, and you had to drop what you were doing. How did you handle it?

What they are checking: actual comfort with the fast-paced, shifting-priorities environment the posting describes, not just a claim of flexibility

What's a design decision you made that, in hindsight, you'd do differently? What did you learn from it?

What they are checking: self-awareness and whether they actually learn from mistakes rather than deflecting blame

Tell me about a time you disagreed with a trader or a more senior engineer about a technical approach. How did that get resolved?

What they are checking: ability to hold a technical position while working well with non-engineers who have final say on business outcomes

What would you do

If you noticed a trading algorithm was behaving strangely in production right now, in a live market, what's the very first thing you would do?

What they are checking: instinct for risk containment versus curiosity-driven debugging when real money is on the line

Suppose a trader comes to you and says a strategy needs a new feature by end of day, but you know the quick way to build it introduces technical debt. What do you do?

What they are checking: how they balance business urgency against long-term system health, and whether they communicate the tradeoff instead of just deciding alone

About the work

Walk me through a trading system or low-latency component you built. What made performance hard, and how did you measure whether you actually improved it?

What they are checking: whether the candidate has real hands-on experience optimizing systems rather than just describing architecture in the abstract

Say you have a piece of C++ code that's supposed to be lock-free but you're seeing occasional data corruption under load. How would you go about tracking that down?

What they are checking: depth of concurrency and memory model knowledge, since correctness bugs in trading systems are expensive

How would you explain the tradeoffs between C++, Python, and Java for different parts of a trading system?

What they are checking: whether the candidate understands why each language is used where it is, not just that they've used all three

How do you approach testing code that touches live trading logic, where you can't just run it against production to see what happens?

What they are checking: rigor around testing methodology in a domain where mistakes are costly and hard to reverse

How do you think about garbage collection or memory management differences when moving logic between Java and C++ components in the same system?

What they are checking: whether their cross-language experience is genuine and detailed, given the job explicitly requires all three languages

How would you design a system to handle a sudden spike in market data volume without falling behind or dropping messages?

What they are checking: systems design ability specific to high-throughput, low-latency trading infrastructure

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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.  Our collaborative culture fuels innovation in quantitative research, systematic trading strategies, and cutting-edge trading technology.  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.   RESPONSIBILITIES • Design, develop, and maintain high-performance trading systems and algorithms, utilizing languages such as C++, Python, and Java • Minimum of 4 years working experience in software development, preferably within a large distributed computing or systematic trading environment • Bachelor's degree in Computer Science or quantitative field • Comfortable working in a fast-paced, dynamic environment, adapting quickly to changing priorities and demonstrating flexibility in handling various tasks and projects COMPENSATION • Salary Range: $145,000 - $225,000, plus a discretionary bonus. • The discretionary bonus will be dependent upon the individuals skills, experience, qualifications, and firm performance.    Most teams at CTC, with the exception of Trading, follow a hybrid workplace model, subject to change based on business need. Our Benefits  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.  (Disclaimer: interns and contractors are not eligible for benefits at CTC)  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.  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.

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