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Senior Software Engineer, Cumberland/Options Data

DRW · Chicago, IL · 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

Tell me about a data platform you helped scale. What broke first as volume grew?

What they are checking: Real experience with scaling limits and how they addressed them.

How do you work with traders and researchers to understand what data they actually need?

What they are checking: Turning vague requests into useful data products through good questions.

How do you mentor engineers and set standards on a data engineering team?

What they are checking: Senior-level influence on code quality and practices across the team.

What would you do

Crypto markets never close. How does that shape how you deploy and maintain data systems?

What they are checking: Operating without maintenance windows, including zero-downtime deployment and backfill strategies.

A researcher says two datasets disagree on the same trade. How do you resolve it?

What they are checking: Careful root cause investigation and clear communication about which data to trust.

About the work

The team builds datasets and APIs for crypto and options trading at large volumes. How would you design an API that serves fast queries over years of tick data?

What they are checking: Data system design focused on storage layout, indexing and access patterns for heavy time series use.

How do you guarantee data quality and integrity when ingesting from many venues at once?

What they are checking: Concrete validation, reconciliation and monitoring practices for high-volume pipelines.

How would you model options reference data so contracts across different venues map cleanly?

What they are checking: Understanding of symbology, contract specs and reference data challenges in options and crypto.

What's your approach to making pipelines idempotent and safe to rerun?

What they are checking: Defensive pipeline design that makes recovery from failures safe and simple.

What would you monitor to know your data platform is healthy?

What they are checking: Thinking in terms of freshness, completeness and latency that matter to data consumers.

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. About the Team The DRW C/Options Data Engineering team is essential to developing valuable datasets and scalable data infrastructure critical to our trading operations. We work closely with traders, researchers, and other engineering teams to ensure seamless data flow and accessibility, supporting data-driven decision-making. Our systems are designed to handle large volumes of data, maintain quality and integrity, and provide robust APIs for fast, ergonomic data retrieval. About the Role In this role you will: • Collaborate with cross-functional teams to deliver data solutions that support diverse trading activities. • Take full ownership of data products, guiding them from initial concept through to stable production. • Design, build, and maintain systems for both batch processing and real-time streaming of time series datasets, ensuring high data quality and reliability. • Develop APIs and data access methods for fast, intuitive retrieval of historical and live data, working with both new and existing systems. • Provide on-call support as needed. Qualifications: • A minimum of 2+ years’ experience using at least one of Python, Java, and C++, 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 pipeline orchestration frameworks (e.g. Airflow, Dagster) • Experience with streaming platforms (e.g. Kafka), data lake platforms (e.g. Delta Lake, Apache Iceberg), and relational databases • 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 $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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