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Software Engineer - Cumberland/Options Front Office Systems

DRW · Chicago, IL · $175,000–$225,000 a year · FICC Options Infrastructure, Tools, & Analytics

Posted Sep 30, 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

The team turns alpha signals, risk tools and market visualizations into production systems for traders. Tell me about a time you took a trader's or researcher's prototype and made it production-ready.

What they are checking: Whether they can harden someone else's idea without losing what made it valuable.

Tell me about a production system you built that had to be both fast and correct. Which did you trade off, and how?

What they are checking: Their judgment about performance versus correctness when real money is at stake.

Tell me about a time you had to learn a new domain quickly to be useful.

What they are checking: Learning speed and curiosity, which matter for a team that embeds with traders.

What would you do

We move quickly when we prototype and tread lightly when we ship to production. How do you change your habits between those two modes?

What they are checking: Whether they know which shortcuts are fine in a prototype and which become dangerous in production.

A trader sitting next to you asks for a feature today that conflicts with what another trader asked for yesterday. What do you do?

What they are checking: Whether they can embed closely with users while still managing priorities and raising conflicts openly.

About the work

How would you compute and serve real-time greeks for a large crypto options book?

What they are checking: Understanding of options pricing inputs and the engineering of recomputing many values quickly as markets move.

Walk me through how you would design a dashboard that shows traders their risk across crypto options positions as it changes.

What they are checking: Thinking about data freshness, update rates and what a trader actually needs to see at a glance.

Crypto trades 24/7. How does that change the way you design, deploy and support systems?

What they are checking: Awareness that there is no overnight window, so deploys, failover and on-call must be planned differently.

How would you explain implied volatility to someone new to options?

What they are checking: Whether they understand the business well enough to talk with traders in their terms.

How do you test a signal or risk calculation so you trust it before traders rely on it?

What they are checking: Use of reference values, backtests and comparisons to catch errors before they reach trading.

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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. About the Team DRW C/Options Front Office Systems team intimately collaborates with traders to turn alpha signals, risk management, market visualizations and other trading-critical tools into scalable, performant and reliable production systems. We embed deeply with our customers to solve high-impact, complex problems. We move quickly when we prototype, and we tread lightly when we ship to production.  We operate at the intersection of ensuring customer success and creating quality products that stand the test of time. We work closely with Data Engineering, Research Engineering, and Execution Engineering. About the Role Software Engineers in Front Office Systems operate in two very distinct but organically interconnected modes. • During a Forward Deployment, you will be directly embedded onto a trading desk, where you will be tasked to navigate business context, ambiguity in requirements, trade-offs, and urgency to deliver. You will promote a mutually beneficial relationship with the trading desks by building them specialized solutions to solve their greatest problems, while at the same time building up domain specific knowledge. • After returning from a Forward Deployment, you will leverage the knowledge you gained from the process, extract reusable patterns, and make the tools available for all trading desks. In this role you will: • Work with best-in-class trading tools for a collection of Cumberland and FICC options trading desks • Take full ownership of the products you create, from prototype to stable production • Embed with trading desks, learn about their problem spaces, extract domain models, and build ergonomic, performant and extendable engineering solutions • Build, maintain and extend the central trading platform • Work with both greenfield and legacy systems across multiple languages (C++, Python, Typescript)  • Provide on-call support as needed Qualifications: • Up to 7 years of experience using C++ and Python and can work comfortably in multiple programming languages • A track record of working directly with end customers, scoping and delivering production systems in fast-moving and ambiguous environments • Ability to dive deep into complex problems, develop intuitive understandings, spot risks early, and minimize complexity • Exceptional interpersonal skills - you communicate clearly with stakeholders as well as other engineers, fostering a collaborative, supportive working environment. • Experience in the financial markets, especially in delta one store of value and/or FICC options trading • Experience with linux-based, concurrent, high-throughput, low-latency software systems • Experience with functional programming is a plus • Have a Bachelors or advanced degree in Computer Science, Mathematics, Statistics, Physics, Engineering, or equivalent work experience   The annual base salary range for this position is $175,000 to $225,000 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-BL1

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