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Trade Support Specialist - Cumberland Options

DRW · Chicago, IL · $90,000–$130,000 a year · FICC Options Middle Office

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 manual process you automated or improved with a tool or script.

What they are checking: Whether they use technology to improve workflow, which the posting highlights.

Tell me about a time you caught an error before it became a costly problem.

What they are checking: Attention to detail and a habit of checking, which protects the firm's capital.

How do you build trust with traders, engineers and researchers who each want different things from you?

What they are checking: Whether they can be a reliable partner to several groups in a fast-moving desk environment.

What would you do

A position in our system does not match what the exchange shows. How do you track down the break?

What they are checking: A methodical process for finding missing, duplicated or misbooked trades before they cause risk errors.

Crypto markets trade around the clock. How would you keep operations reliable outside normal hours?

What they are checking: Whether they think about coverage, automation and handoffs for a market that never closes.

A trader asks you to fix something urgently while you are in the middle of month-end reconciliation. What do you do?

What they are checking: Prioritization under pressure and clear communication about what will slip.

About the work

You will support several crypto trading desks. What happens between a trade being executed and it being fully reconciled?

What they are checking: Understanding of trade capture, booking, confirmation and reconciliation, the core of operational support.

How do crypto options differ operationally from listed equity options?

What they are checking: Awareness of settlement, venues, collateral and expiry differences that affect day-to-day support.

What do you know about how options expire and settle, and what could go wrong at expiry?

What they are checking: Knowledge of exercise, assignment and settlement risks that make expiry a high-stakes day.

How comfortable are you with SQL or Python for pulling and checking trade data?

What they are checking: Whether they can work with data directly instead of relying only on spreadsheets.

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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 , Cumberland Options you will provide 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 support for several of the firm’s crypto trading desks • Trade capture for all products related to the desks’ activity: futures/futures 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 or working knowledge and experience in crypto • Previous experience with Version Control, Git, Python, Cron, Linux • 2-3 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 • Experience working with derivatives is preferred • Substantial prior interaction with the front office and senior management in an active trading environment • Bachelor’s degree in finance, economics, computer science, 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 $90,000 to $130,000 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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