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Service Reliability Engineering Technical Lead

DRW · Chicago, IL · $250,000–$300,000 a year · IO - Container Infrastructure

Posted Oct 2, 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 time you led a team through a major platform change. How did you get buy-in from the engineers and from the users?

What they are checking: Their ability to lead by persuasion and planning rather than by mandate.

How do you balance roadmap work against interrupts and support requests from many teams?

What they are checking: Whether they protect project time with clear intake and on-call rules so the team does not drown in tickets.

How do you raise the skill level of the engineers on your team?

What they are checking: Whether they invest in reviews, pairing and design discussions that grow people, not just ship work.

Describe a time you disagreed with a senior stakeholder about a technical direction.

What they are checking: Whether they can challenge consensus with evidence, which the firm says it wants, and still commit once decided.

What would you do

As technical lead for Container Infrastructure, how would you set the direction for on-prem and cloud orchestration over the next year?

What they are checking: Whether they can form a technical roadmap tied to what desks and data scientists actually need.

One of your engineers wants to rewrite a working component because it is ugly. How do you handle it?

What they are checking: Whether they weigh the business value of a rewrite against risk while keeping the engineer engaged.

About the work

How would you design a multi-cluster Kubernetes setup that spans on-premises and cloud?

What they are checking: Depth in federation, workload placement, networking and failure isolation across environments.

The team favors off-the-shelf tools with just enough engineering. How do you decide when to adopt an open-source project versus building your own?

What they are checking: Judgment about community health, operational cost and fit before committing the team to a tool.

Walk me through how you would run a blameless postmortem after an outage that hurt a trading desk.

What they are checking: Whether they find system causes and drive follow-through without letting blame or hindsight distort the review.

What metrics would you use to show leadership that the container platform is healthy and worth investing in?

What they are checking: Ability to translate reliability and adoption into measures that non-engineers can act on.

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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. The Container Infrastructure team provides scalable on-premises and cloud-based container orchestration services for DRW’s trading desks, data scientists, and enterprise application teams. Our goal is to enable teams to keep focused on their business goals by providing simple, scalable solutions with off the shelf tools and the right amount of focused engineering. We're looking for a Technical Lead for our Container Infrastructure team. In this role you work closely with other teams and trading desks to ensure the performance and reliability of our Kubernetes platform. The platform is large: hundreds of clusters, thousands of nodes, and dozens of components. Common day-two tasks include development of new components, monitoring costs, and ensuring compute consumption for each desk is optimized. The Technical Lead is responsible for key design of architectural decisions for our platform, setting engineering standards, prioritizing and assigning technical work, as well and identifying and eliminating risks and technical debt. Our philosophy: • We believe in relentless automation of repetitive tasks. • We have the curiosity and drive to dig deep and find creative solutions. • We believe our goal is to find the right solution rather than always being right. • We provide exceptional customer service to our teams and trading desks. • We care more that the right thing is done than about rigid job descriptions or boundaries. What you’ll do: • Own and improve infrastructure, processes, and standards for DRW’s Kubernetes platform. • Work with different business units to ensure a successful onboarding and deployment of applications into DRW’s Kubernetes platform. • Promote DRW’s Kubernetes platform with demos, lightning talks, and presentations. • Relentlessly automate repetitive manual tasks. • Provide exceptional customer service to our platform’s users. • Coach engineers on best practices, help solve complex problems, set a high standard for operational and technical excellence Your background: • Multiple years of Kubernetes administration experience. • Deep knowledge of networking, storage, and containerization fundamentals • Familiarity with AWS and/or Google Cloud Platform. • A service focused attitude: you ask questions and focus on getting the right resources and solutions to people instead of rigid boundaries. • Strong written and verbal communication skills. You can work across teams and have evidence-based discussions on technical and operational topics • You enjoy leading by example. You cultivate technical excellence and soft skills in your team members. Bonus points if you have: • Experience with common Kubernetes operators (Flux, Fluentbit, Fluentd, Prometheus, etc.) • Experience administering on-premise infrastructure. • Experience developing, deploying, and supporting full stack web applications. • Experience with multiple programming languages in both greenfield development and legacy maintenance. The annual base salary range for this position is $250,000 to $300,000 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-SK1]  

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