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Software Engineer, Research – Cumberland Systematic

DRW · Chicago, IL · $175,000–$225,000 a year · Cumberland Engineering & DevOps

Posted Oct 1, 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 works across Chicago and London. How do you keep collaboration and handoffs smooth across time zones?

What they are checking: Whether they write clearly and document so work does not stall while the other office sleeps.

You are expected to work across the full stack. Tell me about a time you worked well outside your strongest area.

What they are checking: Range and willingness to pick up whatever the team needs.

Tell me about a time you made a data-heavy job much faster.

What they are checking: Practical performance skills in the kind of large-data work research depends on.

What would you do

A strategy behaves differently in production than it did in research. How do you find out why?

What they are checking: A structured approach comparing data, latency, fills and code versions to locate the gap.

About the work

Cumberland Systematic trades mid and high-frequency delta one strategies 24/7. What does high availability mean for a system like that, and how would you design for it?

What they are checking: Whether they understand failover, redundancy and state recovery when there is no market close to fix things.

Walk me through how you would build a research pipeline that lets quants backtest strategies on large amounts of tick data.

What they are checking: Design for data storage, reproducibility and speed that matches how researchers actually work.

How do you make sure a backtest and live trading use the same logic so results are trustworthy?

What they are checking: Awareness of look-ahead bias, timing differences and shared code paths that make research honest.

What is delta one, and why might a systematic team trade it on crypto venues?

What they are checking: Basic understanding of the products the team trades, so they can talk with researchers in their terms.

How would you handle a crypto exchange connection that drops and reconnects with gaps in market data?

What they are checking: Thinking about sequence gaps, snapshots and keeping strategies safe while data is incomplete.

How do you decide which language or tool to use for a new research component?

What they are checking: Whether they pick tools for the job and the team, weighing speed of development against runtime speed.

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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. Cumberland Systematic  is a multi-asset trading team focused on mid and high-frequency fully systematic strategies in the delta one space. We trade 24/7 globally with our team located primarily in Chicago and London. We are looking for a Software Engineer to join our team. You will work with other software engineers to design and develop the full stack needed to enable a global trading operation with high availability requirements. You will be expected to design and develop integrations with data vendors, blockchain infrastructure, data management solutions, and libraries for managing and analyzing data. The team’s existing systems are written in Python and C++. Candidates should have strong initiative and proven experience independently driving projects to completion. We work from high-level requirements and engineers are expected to gain an intimate understanding of the business and work directly with quantitative researchers on a daily basis. Responsibilities: • Design, develop, test, document, and maintain software and infrastructure needed for quantitative financial research • Accelerate the research lifecycle from data engineering to feature generation and analysis • Integrate with diverse data sources such as blockchains, exchanges, and data vendors • Test at the unit, functional, and integration levels • Work within in a small team as well as independently with a strong user focus • Provide on-call support as needed To qualify for this role, you must have: • Python experience gained through professional experience • Built complex systems in modern Python that are maintainable and safely refactorable • Hands-on experience managing large, evolving timeseries data • A working knowledge of type safety and type systems • Strong verbal and written communication skills • Strong internal motivation and a continual desire to learn Bonus points if you have: • Contributions to open-source crypto projects • Production experience running full or archive blockchain nodes at scale • Collaborated with quantitative researchers • A working knowledge of high-level machine learning concepts and lifecycle • Experience with functional programming and immutable design principles • Practical knowledge of major blockchain types and clients 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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