Department: Technology
Employment Type: Full Time
Location: Chicago, IL
Description
We are seeking an accomplished and seasoned Information Systems Manager to lead our Information Systems and Helpdesk teams in a demanding, high-availability proprietary trading environment. This role blends hands-on technical expertise with strong leadership and communication skills. You will own and oversee enterprise systems that support critical trading and business operations, ensuring reliability, performance, and security across the firm's infrastructure.
What You'll Do
- Lead and develop the Information Systems and Helpdesk teams, setting technical direction and driving growth through mentorship and a culture of accountability.
- Oversee core enterprise services including Active Directory, DNS, DHCP, Exchange, Microsoft 365, endpoint threat protection, backups and enterprise file/storage infrastructure.
- Architect and manage the firm's Microsoft cloud ecosystem, spanning identity and access management, compliance and data governance, cloud infrastructure, and hybrid connectivity, ensuring seamless integration with on-premises systems.
- Drive the adoption and governance of Microsoft 365 productivity and AI capabilities, evaluating and operationalizing features that meaningfully improves business workflows.
- Architect, manage and optimize VMware environments to ensure scalable, resilient and high-availability virtualization platforms.
- Execute major system initiatives-including deployments, migrations, and upgrades-ensuring operational continuity and effective coordination with other technology teams.
- Design and execute strategies for Windows OS lifecycle management, including versioning, patching, hardening and modernization.
- Partner closely with Network and Security teams to maintain a robust, secure, compliant, and high-performing environment.
- Manage Cisco Unified Communications, Webex, and associated collaboration platforms.
- Serve as the top-tier escalation point for complex infrastructure and helpdesk issues.
- Drive initiatives in system monitoring, performance tuning, and incident response to meet the low-latency and high-availability requirements of our system.
- Promote best practices in system security, access control, and change management, aligned with trading-industry requirements.
- Participate in long-term infrastructure planning, capacity management, and technology road-mapping with senior leadership.
What We're Looking For
- 8+ years of progressive operational IT experience supporting mission-critical environments.
- Bachelor's degree in Engineering, Computer Science, Information Systems, or an equivalent technical field.
- 2+ years leading or managing systems engineering or infrastructure teams.
- Deep expertise in Microsoft Server ecosystem: Active Directory, Exchange, DNS/DHCP, Group Policy, and endpoint management systems
- Strong hands-on experience across the Microsoft cloud ecosystem, including identity and access management, compliance and data governance, and hybrid identity integration with on-premises Active Directory environments.
- Demonstrated ability to manage and evolve a Microsoft 365 tenant, including security posture, administrative governance, and the rollout of AI-Powered productivity capabilities.
- Demonstrated success delivering major system deployments, upgrades, and infrastructure transformations.
- Strong hands-on proficiency with VMware, enterprise AV platforms, backup solutions, and enterprise storage systems
- Familiarity with Cisco Unified Communications, Webex, and modern collaboration tools.
- Strong collaboration skills with good understanding of networking fundamentals, and the ability to troubleshoot and collaborate effectively with network engineers.
- Experience supporting fast-paced financial or trading environments strongly preferred.
- Microsoft certifications strongly preferred, particularly in Microsoft 365 administration, identity and access management, or Azure infrastructure.
- VMware certifications are highly desirable.
Why Join Us
Our flat organizational structure promotes teamwork across the Firm and offers easy access to senior staff. While we work exceptionally well as a team in the office, our bonds are further strengthened through company events, activities and giving back. Volleyball, soccer, hockey, 5K runs, picnic, parties, and trivia nights provide friendly competition and build better relationships. By getting out of our usual environment and doing out-of-the-ordinary things together, we foster creativity and broaden our imaginations to accomplish new challenges.
Benefits:
- Highly competitive salary & bonus opportunity
- Generous paid time off and flexible scheduling
- 100% coverage of medical, dental, vision, life, and disability benefits for single coverage
- Generous Paid Parental Leave
- Retirement Plans: 401K and Roth 401K
- Profit sharing plan
- Long- and short-term disability
Additional Perks:
- Free breakfast and lunch from our in-house kitchen with rotating menus (including snacks!)
- On-site gym with a subsidized membership
- Frequent company outings
- Opportunity to give back to organizations that help individuals in need in the Chicagoland area
Professional Development:
- In-house education team - classes and resources are offered for continuous learning opportunities
- Mentorship Program through your first six months of employment
The base compensation range for this role is approximately $125,000-$175,000 contingent on experience. Wolverine Trading's total compensation model includes base salary and an annual discretionary bonus.
Skills Required
- 8+ years of operational IT experience supporting mission-critical environments
- Bachelor's degree in Engineering, Computer Science, Information Systems, or equivalent
- 2+ years leading or managing systems engineering or infrastructure teams
- Deep expertise in Microsoft Server ecosystem
- Strong hands-on experience with Microsoft cloud ecosystem
- Demonstrated ability to manage and evolve a Microsoft 365 tenant
- Strong hands-on proficiency with VMware and enterprise storage systems
- Familiarity with Cisco Unified Communications and modern collaboration tools
- Experience supporting fast-paced financial or trading environments
- Microsoft certifications preferred, particularly in Microsoft 365 and Azure infrastructure
Wolverine Trading Compensation & Benefits Highlights
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Healthcare Strength — Employer materials list medical, dental, vision, life, and both short‑ and long‑term disability, and feedback suggests premiums for singles are often fully or heavily covered with HSA support. Plan transparency and named carrier signals organized, established coverage options.
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Retirement Support — Plan offerings include 401(k) and Roth 401(k) alongside a profit‑sharing plan, indicating meaningful long‑term wealth support. Feedback suggests retirement features are a notable component of total rewards.
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Wellbeing & Lifestyle Benefits — Daily chef‑prepared meals, a subsidized on‑site gym, and frequent social events are positioned as core perks enhancing day‑to‑day experience. These amenities reduce out‑of‑pocket costs and support workplace community.
Wolverine Trading Insights
What We Do
The Wolverine companies comprise a number of diversified financial institutions specializing in proprietary trading, asset management, order execution services, and technology solutions. We are recognized as a market leader in derivatives valuation, trading, and value-added order execution across global equity, options, and futures markets.
Why Work With Us
At Wolverine, we've created a strong, collaborative environment with exceptional growth opportunities. Whether your interest is trading, technology, or operations, motivated and innovative individuals can find many pathways to success. Our flat organizational structure promotes teamwork across the Firm and offers easy access to senior staff.
Gallery
Wolverine Trading Offices
OnSite Workspace
We believe that some of our best work is done working alongside each other at our Chicago headquarters. Whether we are sharing a meal prepared by our in-house culinary team or whiteboarding problems, the opportunities to collaborate are endless.

