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Enterprise Infrastructure Engineering Lead

Optiver · Chicago, IL · 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 team of infrastructure engineers you have led. How did you balance leading with staying hands-on?

What they are checking: Whether they can do both, since the posting wants strategic leadership and deep technical expertise together.

The posting describes being a culture carrier. What team habits would you build or protect?

What they are checking: Whether they think deliberately about team culture, communication and ways of working.

Tell me about a time you had to give an engineer difficult feedback.

What they are checking: Whether they handle people issues directly and fairly, which leading a small high-performing team requires.

What would you do

You would own the global Optiver Trading Workstation infrastructure. What matters most when traders' desktops are the product?

What they are checking: Whether they understand that workstation reliability and speed directly affect traders' ability to work.

A NetApp storage issue slows down several critical systems. How do you lead the response?

What they are checking: Whether they can lead an incident calmly, communicate well and drive a fix and a follow-up review.

How do you work with infrastructure teams in other offices when you have different priorities?

What they are checking: Whether they can collaborate globally and reach agreement without forcing a Chicago-only view.

About the work

How would you roll out a change to trading workstations without disrupting traders during market hours?

What they are checking: Whether they plan staged rollouts, testing and timing around markets to avoid harming trading.

Walk me through how you would use Terraform, Python or PowerShell to manage VMware and Windows Server infrastructure as code.

What they are checking: Whether they can automate real enterprise infrastructure, not just cloud resources.

How do you decide what infrastructure should stay on-premises and what should move to the cloud?

What they are checking: Whether they weigh latency, cost, security and control in a hybrid environment like this one.

How do you keep enterprise infrastructure secure without slowing engineers down?

What they are checking: Whether they build security into automation and standards rather than adding manual gates.

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The full job description

As published by Optiver.

Optiver is looking for an experienced and hands-on Infrastructure Lead to join our US Enterprise Infrastructure Engineering team in Chicago. In this role, you’ll lead a small team of high-performing engineers, drive technical initiatives across our hybrid infrastructure, and collaborate closely with global stakeholders. You’ll be responsible for both technical delivery and team development — striking the balance between strategic leadership and deep technical expertise. We’re looking for someone who thrives in a dynamic, fast-paced setting and is passionate about building scalable, secure, and automated infrastructure solutions. What you'll do • Lead and mentor a team of infrastructure engineers based in Chicago • Develop and manage the global Optiver Trading Workstation infrastructure. You’ll directly influence the front-end systems used by all traders in Optiver • Drive automation and infrastructure-as-code best practices using tools like Python, PowerShell, and Terraform • Own critical systems across VMware, Windows Server, NetApp, and related enterprise infrastructure • Collaborate with cross-functional teams globally, ensuring reliability, scalability, and operational excellence • Be a culture carrier — shaping team values, communication practices, and ways of working • Influence long-term technical direction and provide strategic input on how infrastructure evolves to meet business needs • Ensure observability and proactive system monitoring across all platforms What you'll get You’ll join a culture of collaboration and excellence, surrounded by curious thinkers and creative problem-solvers. Motivated by a passion for continuous improvement, you’ll thrive in a supportive, high-performing environment alongside talented colleagues, collectively tackling some of the toughest challenges in the financial markets. In addition, you’ll receive: • The opportunity to work alongside best-in-class professionals from over 40 different countries • Highly competitive compensation package including performance-based bonus structure • 401(k) match up to 50% • Comprehensive health, mental, dental, vision, disability, and life coverage • 25 paid vacation days alongside market holidays • Extensive office perks, including breakfast, lunch and snacks, regular social events, clubs, sporting leagues and more Who you are • Proven leadership experience managing or mentoring technical teams (minimum 3+ years in a lead capacity) • Strong technical background in infrastructure engineering • Deep hands-on experience with, or a willingness to learn and dive deep into: • Python, PowerShell, or Terraform (HCL) • Virtualization infrastructure • Windows Server management & debugging • NetApp or similar enterprise storage systems • Solid understanding of Active Directory, DNS, and core networking concepts • Experience with observability stacks (e.g., SCOM, Telegraf/Influx/Grafana, Prometheus) • Strategic thinker with the ability to influence and drive decisions, with a high degree of ownership • Strong listener who creates space for diverse views while providing technical direction Who we are At Optiver, our mission is to improve the market by injecting liquidity, providing accurate pricing, increasing transparency and stabilizing the market no matter the conditions. With a focus on continuous improvement, we prioritize safeguarding the health and efficiency of the markets for all participants. As one of the largest market making institutions, we are a respected partner on 100+ exchanges across the globe. Our differences are our edge. Optiver does not discriminate on the basis of race, religion, color, sex, gender identity, sexual orientation, age, physical or mental disability, or other legally protected characteristics.   Below is the expected base salary for this position. This is a good-faith estimate of the base pay scale for this position and offers will ultimately be determined based on experience, education, skill set, and performance in the interview process. This position will also be eligible for a discretionary bonus (if determined by Optiver) and Optiver’s benefits package with the benefits listed above.    Base Salary Range $200,000 — $230,000 USD

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