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Trade Support Specialist - Middle Office

DRW · Chicago, IL · $100,000–$125,000 a year · FICC Options

Posted Aug 19, 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 improved a workflow using a tool, script or better process.

What they are checking: Whether they look for better ways to work, which the role explicitly asks for.

Tell me about a mistake you made at work. How did you handle it?

What they are checking: Honesty and speed in raising errors, which matters more than never making one.

Why middle office at a proprietary trading firm?

What they are checking: Real interest in markets and operations rather than seeing the role as a stopgap.

What would you do

Our P&L and the clearing firm's statement are off by a meaningful amount. How do you find out why?

What they are checking: A structured approach to breaks across trades, prices, fees and corporate actions.

A trader disputes a fill and says it was booked wrong. How do you handle it?

What they are checking: Calm investigation using records and fair communication, even when a trader is frustrated.

Several desks need things from you at once near the close. How do you decide what comes first?

What they are checking: Whether they rank tasks by risk and deadline, not by who is loudest.

About the work

You will support equity options trading desks. Walk me through the middle office checks you would run at the end of each trading day.

What they are checking: Knowledge of trade, position and P&L reconciliation that keeps the books right.

How does a corporate action like a stock split affect an options position?

What they are checking: Understanding of contract adjustments, which commonly cause errors in options books.

What happens to equity options on expiration Friday, and what can go wrong operationally?

What they are checking: Awareness of exercise and assignment, pin risk and the deadlines that make expiry demanding.

How would you use SQL or Python to spot trades that look unusual or misbooked?

What they are checking: Practical data skills that let them check large volumes instead of eyeballing.

Practice this interview out loud.

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The full job description

As published by DRW.

DRW is a diversified trading firm with over 3 decades of experience bringing sophisticated technology and exceptional people together to operate in markets around the world. We value autonomy and the ability to quickly pivot to capture opportunities, so we operate using our own capital and trading at our own risk. Headquartered in Chicago with offices throughout the U.S., Canada, Europe, and Asia, we trade a variety of asset classes including Fixed Income, ETFs, Equities, FX, Commodities and Energy across all major global markets. We have also leveraged our expertise and technology to expand into three non-traditional strategies: real estate, venture capital and cryptoassets. We operate with respect, curiosity and open minds. The people who thrive here share our belief that it’s not just what we do that matters–it's how we do it. DRW is a place of high expectations, integrity, innovation and a willingness to challenge consensus. As a  Trade Support Specialist , you’ll provide middle office support to a group of trading desks based in Chicago. This is an opportunity to solve challenging problems while working closely with experienced traders, researchers and software engineers to optimize operational workflow and use the right tools and technology for the job. Responsibilities: • Provide operational and technical support for the firm’s equity options trading desks • Trade capture for all products related to the desks’ activity: futures/futures options, equities/equity options, index options • Trade and position reconciliation with the firm’s clearing houses and brokers • Daily P&L calculation and substantiation • Working knowledge and experience in derivatives • Gain mastery of the firm’s proprietary trade capture, inventory management, treasury management, and risk management systems necessary to support the desks’ activity • Act as process owner for current functionality and provide critical support and advice regarding needed enhancements to technology, workflows, and processes: • Gain a strong understanding of traders’ risk management tools and provide support for related traders’ needs • Upgrade and support traders’ tools to effectively utilize technologies and tools that are firm standard • Interface with technology to improve tools where they fall short of meeting the desks’ needs • Adopt, integrate, and promote new technology as it becomes available  Requirements: • Strong interest in, and working knowledge of equities and derivatives • Experience with Version Control, Git, Python, Cron, Linux • Proven experience automating or improving workflows using Python • 3+ years of experience in the front office, middle office, back office, or risk management roles working with exchange-traded and over-the-counter products and derivatives • Substantial prior interaction with the front office and senior management in an active trading environment • Bachelor’s degree in computer science, finance, economics, math, or another quantitative field or material equivalent exposure • Demonstrated ability to work independently • Demonstrated ability to analyze problems and synthesize and implement solutions The annual base salary range for this position is $100,000 to $125,000 depending on the candidate’s experience, qualifications, and relevant skill set. The position is also eligible for an annual discretionary bonus. In addition, DRW offers a comprehensive suite of employee benefits including group medical, pharmacy, dental and vision insurance, 401k (with discretionary employer match), short and long-term disability, life and AD&D insurance, health savings accounts, and flexible spending accounts. For more information about DRW's processing activities and our use of job applicants' data, please view our Privacy Notice at https://drw.com/privacy-notice . California residents, please review the California Privacy Notice for information about certain legal rights at https://drw.com/california-privacy-notice . [#LI-TL1]  

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