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Senior Systems Engineer

DV Trading · Chicago, IL · Technology

Posted Sep 15, 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 infrastructure automation you built for deploying on-premises and cloud resources.

What they are checking: Hands-on use of tools like PowerShell, Terraform or Ansible, which the posting stresses.

Tell me about a time you introduced a new technology to improve IT operations.

What they are checking: Whether they drive improvements thoughtfully, with testing and buy-in.

How do you mentor junior engineers on a growing IT team?

What they are checking: Whether a senior hire shares knowledge and grows others so the team does not depend on one person.

What would you do

You would partner with Security on centralized identity and access management. How would you approach that work?

What they are checking: Ability to collaborate on identity design while balancing security and usability.

A Windows update breaks a critical trading application on many desktops. What do you do?

What they are checking: Fast rollback, communication with users and a better patching process afterward.

About the work

You would design and maintain Windows Server and desktop environments. Walk me through how you would standardize desktop builds across Chicago, New York and London.

What they are checking: Experience with imaging, configuration management and consistency across offices.

What virtualization and cloud platforms have you designed, and what trade-offs did you make?

What they are checking: Depth in choosing between on-prem and cloud for different workloads.

How would you design backup and recovery for Windows servers and virtual machines?

What they are checking: Understanding of recovery objectives, testing restores and protecting against ransomware.

How do you keep Active Directory healthy across multiple sites?

What they are checking: Knowledge of replication, sites and DNS that matter in a multi-office firm.

How would you control costs in a cloud environment?

What they are checking: Awareness of right-sizing, tagging and monitoring spend as cloud use grows.

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The full job description

As published by DV Trading.

About Us : Founded 20 years ago and headquartered in Chicago, the  DV Group of financial services firms has grown to more than 600 people operating throughout North America, Europe and Asia. Since spinning out of a large brokerage firm in 2016, DV Trading has rapidly scaled as an independent proprietary trading firm utilizing its own capital, trading strategies, and risk management methodologies to provide liquidity to worldwide financial markets and hedging opportunities to commodity producers and users. Now, DV group affiliates include two broker dealers, a cryptocurrency market making firm, and a bourgeoning investment adviser. Overview: DV is looking for a Senior Systems Engineer, working out of either our Chicago, New York, or London office, to join a growing IT organization that will help impact our Windows, virtualization, and cloud capabilities. In this role you will work on driving our core infrastructure forward, leveraging the latest and greatest technologies to help improve our IT operations. Job Responsibilities: • Design, build and maintain Windows Server and Desktop environments   • Design, build and maintain virtualization and cloud environments    • Leverage automation for deploying and supporting on-premises and cloud infrastructure     • Partner with the Security team on the design, implement, and support of our centralized identity and access management solution   • Partner with the Security team to ensure we are adhering to security best practices across all environments including patch remediation and system hardening   • Review and improve upon existing monitoring systems and process     • Perform Windows OS performance tuning     • Author and maintain computer system design documentation, diagrams, processes and procedures    • Promote and adopt Infrastructure as Code across all IT   • Be a mentor to junior IT staff   • Participate in an on-call rotation Requirements: • Self-starter with a passion for technology and problem solving   • Experience as a senior infrastructure engineer   • Deep knowledge and practical implementation of Windows, virtualization, and cloud computing infrastructure     • Deep knowledge of Windows operating systems   • Deep knowledge of virtualization technologies   • Experience implementing and supporting identity platforms such as Azure AD and Active Directory   • Knowledge of TCP/IP and multicast   • Knowledge of scripting languages such as Powershell and Python    • Extensive experience configuration management systems such as Ansible, Salt, or Terraform   • Extensive experience with endpoint management systems such as Microsoft Endpoint Manager    • Excellent interpersonal and written communication skills   • Ability to present complex, technical ideas in a clear and concise manner to non-technical audiences       Benefits: • Discretionary bonus eligibility • Medical, dental, and vision insurance • HSA, FSA, and Dependent Care Options • Employer Paid Group Term Life and AD&D insurance • Voluntary LTD, Life & AD&D insurance • Flexible Vacation policy • Retirement plan with employer match DV is not accepting unsolicited resumes from search firms. Only search firms with valid, written agreements with DV should submit resumes in response to DV ’s posted positions. All resumes submitted by search firms to DV via e-mail, the Internet, personal delivery, facsimile, or any other method without a valid written agreement shall be deemed the sole property of DV , and no fee will be paid in the event the candidate is hired by DV . DV is proud to be an equal opportunity employer and committed to creating an inclusive environment for all employees. The range below reflects the expected base salary for this position. It represents a good-faith estimate of the base pay we anticipate offering, with actual compensation determined by your experience, education, skills, and performance throughout the interview process. This role is also eligible for a discretionary bonus (at DV Trading's discretion) and DV Trading's benefits package, including the benefits listed above. Base Salary Range $200,000 — $250,000 USD

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