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Cloud Engineer

DRW · Chicago, IL · $175,000–$250,000 a year · IO - Cloud

Posted Sep 10, 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

This role owns the reliability, security and performance of what you deliver. Tell me about something you built that you were fully accountable for.

What they are checking: A track record of end-to-end ownership, which matches a firm that values autonomy and accountability.

Tell me about a time you worked with networking or security teams to ship something that touched all three areas.

What they are checking: Collaboration across infrastructure teams, which the posting says this role does closely.

Describe a production problem you couldn't solve quickly. How did you keep going and what finally cracked it?

What they are checking: Persistence and a methodical debugging approach when the answer is not obvious.

What would you do

A security team flags that a storage bucket was briefly public. What do you do now, and what do you change so it can't happen again?

What they are checking: Calm incident response plus preventive controls, rather than only fixing the single instance.

How do you decide whether a workload should run in the cloud or stay on-prem at a firm like this?

What they are checking: Judgment that weighs cost, latency, data gravity and control instead of assuming cloud is always the answer.

About the work

DRW runs a diverse multi-cloud and hybrid environment. What have you learned about running workloads across more than one cloud provider?

What they are checking: Real experience with the tradeoffs of multi-cloud, not just familiarity with one provider's console.

How do you connect cloud environments back to on-prem data centers securely and with predictable latency?

What they are checking: Practical knowledge of hybrid networking, which matters at a trading firm with significant on-prem systems.

Walk me through how you'd structure infrastructure as code so many teams can use it without stepping on each other.

What they are checking: Ability to design reusable modules and guardrails that scale across many engineering teams.

How do you keep cloud costs visible and under control as usage grows?

What they are checking: Whether they treat optimization as part of the job, which the posting names alongside security and availability.

What does good monitoring look like for a cloud platform that other engineers depend on?

What they are checking: Understanding that platform teams need signals about their internal customers' experience, not just host health.

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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. We are seeking a Cloud Engineer to design, build, and operate DRW's cloud and hybrid infrastructure across a diverse multi-cloud environment, taking ownership and accountability for the reliability, security, and performance of what you deliver. This role helps ensure our cloud infrastructure is secure, highly available, and optimized to support our continued success and growth.  You will partner closely with engineering, security, networking, operations, and business teams to enable appropriate use of public cloud, private infrastructure, and hybrid architectures.  What You'll Do :   • Platform Management:  Manage and evolve cloud platforms, including but not limited to AWS, Microsoft Azure, Google Cloud Platform (GCP), Alibaba Cloud (AliCloud), and Snowflake, along with the associated hybrid and on-premises dependencies required to operate them reliably. • Cloud Foundations:  Design and maintain cloud foundations, including account/subscription/project organization, identity integration (federation, workload identity), policy guardrails, logging, tagging, and shared services. • Operational Excellence:  Serve as the escalation point for complex production and cloud/hybrid-infrastructure issues, owning root cause analysis and holding yourself accountable for durable fixes, engaging cloud provider and partner support teams as needed. • Automation & Standards:  Build and maintain automation, standards, reference architectures, and documentation that strengthen deployment consistency and enable teams to consume cloud services safely and consistently. • Integration & Collaboration:  Engineer and support resilient cloud connectivity, including transit architectures and connectivity between cloud providers and on-premises environments. • Observability & Monitoring:  Implement and improve observability across cloud services, including metrics, logs, traces, alerting, and capacity dashboards. • Stakeholder Support:  Advise application and infrastructure teams on cloud, hybrid, and on-premises architecture choices based on reliability, performance, security, and cost.  • Cost Management:  Partner with Finance and Purchasing on cloud cost visibility, forecasting, and commitments, holding yourself accountable for the team's FinOps and efficiency goals.  • Continuous Improvement:  Research, evaluate, and implement new cloud services and capabilities that improve reliability, developer experience, security, or efficiency.  What We're Looking For:  • 5+ years of experience engineering and administering production cloud environments in multi-cloud and hybrid settings, with strong AWS experience, exposure to one or more of Azure, GCP, Alibaba Cloud (AliCloud), and Snowflake; and integration with on-premises infrastructure.  • Experience with infrastructure as code and automation, including Terraform, Python, APIs/SDKs, CI/CD, and Git.  • Strong knowledge of cloud networking, including VPCs, routing, DNS, firewalls, load balancing, private connectivity, and interconnect providers.  • Working knowledge of cloud security fundamentals, including IAM, encryption/key management, secrets management, and least-privilege design.  • Experience with cloud observability, monitoring, and alerting, and a proven ability to troubleshoot and resolve complex production problems while making sound decisions under pressure.  • Understanding of cloud cost models and practical approaches to cost allocation, optimization, capacity planning, and FinOps.  • Excellent communication and documentation skills, with the ability to learn quickly, take initiative, and adapt to changing technologies and business needs while working effectively across technical teams and cloud providers.  • A proven track record of delivering secure, scalable, and reliable cloud solutions, with strong ownership and accountability for production outcomes.  • Willingness to participate in a 24/7 on-call rotation supporting production cloud environments.  • Previous experience in financial services or trading environments is a plus.  The annual base salary range for this position is $175,000 to $250,000 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-LD1]  

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