Jobs › DRW

Manager, Cloud

DRW · Chicago, IL · $225,000–$275,000 a year · IO - Cloud

Posted Sep 11, 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 cloud team you built or led. How did you hire, and what made it high performing?

What they are checking: Real people leadership experience, including hiring judgment and building a strong team culture.

Describe a major architecture decision you made that you later had to revisit.

What they are checking: Willingness to admit and correct strategic mistakes rather than defend them.

Tell me about a time you had to coach an engineer who was struggling.

What they are checking: Supportive and direct management that improves performance instead of avoiding hard conversations.

How do you keep your own technical judgment sharp as a manager?

What they are checking: Staying credible on architecture decisions while spending most time leading people.

What would you do

Cloud spend jumped 40 percent this quarter and leadership wants to know why. What do you do?

What they are checking: Ability to find cost drivers quickly and explain them clearly to leadership with a plan.

How do you balance your team's roadmap against the constant flow of support requests?

What they are checking: Protecting strategic work while still serving internal customers well.

How would you work with security and networking leaders who have different priorities from yours?

What they are checking: Building partnerships across infrastructure groups, which the posting says this role does closely.

About the work

You'd define the strategy for DRW's multi-cloud environment. How would you decide what belongs in each cloud and what stays on-prem?

What they are checking: A clear framework for placement decisions based on cost, latency, data and control, not vendor preference.

How do you set guardrails so many engineering teams can use the cloud freely without creating security or cost problems?

What they are checking: Platform thinking that makes the safe path the easy path through policy and automation.

What does high availability mean for cloud infrastructure at a trading firm, and how would you test it?

What they are checking: Practical resilience thinking, including failover testing rather than assuming redundancy works.

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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. As Cloud Manager, you will define the strategy, vision, and direction for DRW's multi-cloud environment, overseeing architecture, design, implementation, optimization, and support across the firm while leading a high-performing team of cloud engineers. You will ensure our cloud infrastructure is secure, highly available, and optimized to deliver the performance, scalability, and reliability our continued growth demands.  Partnering closely with engineering, security, and business teams, you will set the standard for operational excellence and innovation across DRW's cloud platforms.  What You'll Do:   • Platform Management:  Lead the design, implementation, and ongoing management of DRW's cloud platforms, including but not limited to AWS, Azure, GCP, Alibaba Cloud, and Snowflake, along with the associated hybrid and on-premises dependencies, applying best practices for performance, security, and availability. • Vision & Strategy:  Own the cloud roadmap and workplan, setting strategic priorities that meet business needs while promoting scalability, sustainability, and innovation. • Team Leadership:  Mentor, grow, and lead a collaborative, high-performing engineering team, including hiring, performance reviews, career development, day-to-day guidance, and holding the team accountable for delivery. • Stakeholder Support:  Serve as the primary point of contact for internal customer teams, delivering cloud solutions that meet their requirements and optimize operational costs. • Integration & Collaboration:  Work closely with security, networking, and other technology groups to engineer resilient cloud connectivity and ensure seamless integration across environments. • Operational Excellence:  Establish proactive observability, monitoring, and alerting, and act as the escalation point for complex production issues. Maintain operational work tracking What We're Looking For:  • 10+ years of technical experience engineering and administering production cloud environments in multi-cloud and hybrid settings, with strong AWS experience and exposure to one or more of Azure, GCP, Alibaba Cloud, and Snowflake.  • 4+ years of experience managing and leading a team of cloud engineers, including performance reviews, mentoring, and workload management.  • Ability to combine strong strategic vision with technical leadership to drive platform evolution.  • A proven track record of delivering secure, scalable, and high-performance cloud solutions in mission-critical environments.  • Strong knowledge of cloud networking, cloud security fundamentals, and infrastructure as code, including Terraform, Python, CI/CD, and Git.  • A service-first approach, delivering highly reliable, utility-grade cloud infrastructure with clear cost visibility and FinOps practices.  • Effective collaboration with peer engineering teams to improve velocity, reliability, and efficiency.  • Excellent communication and stakeholder management skills.  • Previous experience in financial services or trading environments is a plus.  • Willingness to participate in a 24/7 on-call rotation supporting production cloud environments.  The annual base salary range for this position is $225,000 to $275,000 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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