Jobs › DRW

Head of Engineering, Algorithmic Trading Group

DRW · Chicago, IL · $300,000–$500,000 a year · Algo Technology & Software Engineering

Posted Sep 22, 2026 · We last checked this listing on Oct 6, 2026

Apply at DRW

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

You'd lead about 30 experienced software and hardware engineers with long tenure. How do you earn credibility with a team like that in your first months?

What they are checking: Humility and a plan to listen and learn before changing things for a seasoned, stable team.

Describe a production incident in a trading system you were responsible for. What did you change afterward?

What they are checking: Leadership through incidents and building lasting fixes in process and design.

Tell me about a time you had to remove or replace a system people were attached to.

What they are checking: Ability to lead difficult technical change while respecting the people who built the old system.

How do you stay hands-on enough to make good technical calls while leading a team this size?

What they are checking: Staying technically credible as a leader without becoming a bottleneck.

What would you do

Traders want a new feature fast, and your engineers say it needs a major refactor first. How do you decide?

What they are checking: Balancing trading business pressure against long-term system health with clear reasoning.

How do you keep senior engineers engaged and growing when many have been on the team for over a decade?

What they are checking: Thoughtful people leadership that avoids stagnation in a long-tenured group.

About the work

How would you set technical direction across low-latency trading systems, custom hardware and risk management infrastructure?

What they are checking: Ability to see the whole stack and make coherent decisions spanning software, FPGA and risk systems.

Tell me about a time you had to choose between a hardware approach and a software approach for a latency problem.

What they are checking: Real understanding of the tradeoffs in cost, flexibility and speed between FPGAs and software.

How do you make sure risk controls in a low-latency trading system are both fast and trustworthy?

What they are checking: Seriousness about pre-trade risk checks, since failures there can cause large, fast losses.

How do you measure the performance of an algorithmic trading engineering team?

What they are checking: Whether they connect engineering work to trading outcomes and reliability rather than output metrics alone.

Practice this interview out loud.

Offer builds a real interview for this exact role at DRW from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

Practice this out loud

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 crypto assets.   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 willingness to challenge consensus.   About the Role: DRW is seeking a Head of Engineering for the Algorithmic Trading Group to lead the software and hardware engineering effort. The position oversees a collaborative technical team of approximately 30 experienced software and hardware engineers with an average tenure of 10+ years. Key Responsibilities: • Set the technical direction across the full stack, spanning low-latency trading systems, custom hardware, risk management infrastructure, networking, and UX - driving top performance and scalability  • Partner with trading and research teams to balance short-term revenue opportunities against long-term investments in engineering infrastructure • Own production reliability by setting the standards for code quality, testing rigor, and release discipline, with a zero-tolerance approach to production outages • Define the group's strategy for AI adoption, establishing best practices for efficient and safe use • Lead, mentor, and grow the engineering team – attracting top talent and fostering a culture of technical excellence, knowledge sharing, and continuous improvement Qualifications: • 10+ years of progressive experience in software engineering, with at least 5 years in a senior engineering leadership role • Demonstrated track record of building and operating highly reliable, latency-sensitive distributed systems • Proven ability to recruit, develop, and lead high-performing engineering teams of 20+ engineers • Strong familiarity with generative AI coding tools and autonomous agents, with a vision for how to deploy them effectively and safely across engineering workflows • Track record of building and enforcing engineering practices that achieve near-zero defect rates in production  • Bachelor's degree in Computer Science, Engineering, or a related field If this sounds like the right opportunity for you, please provide a resume and a brief statement on your approach to building high-performance, scalable, and extremely reliable systems. The annual base salary range for this position is $300,000 to $500,000 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

Apply at DRW