Senior Windows & Identity Engineer

Chicago-based financial technology firm is seeking a Senior Windows & Identity Engineer to maintain, secure, and modernize the Windows, identity, and endpoint platforms supporting innovative trading, market risk, and broker systems used by clients worldwide.

This role requires a highly motivated, senior-level engineer who will collaborate with a top-tier team of technologists to operate and evolve a secure, highly available, and automated hybrid environment. The position reports to the VP of Hardware and Infrastructure
.

• Manage, support, and troubleshoot enterprise Windows infrastructure including Active Directory, DNS, Group Policy
  , Microsoft Cluster Manager,
  Microsoft Hyper‑V, and hybrid identity platforms
  .
• Design, operate, and support hybrid identity environments
  , including Entra  (Azure AD), Azure AD Connect / Cloud Sync, and device identity lifecycle management.
• Deploy, maintain, and troubleshoot Windows endpoint management platforms
  , including Microsoft Intune and Windows Autopilot
  .
• Install, configure, and maintain hypervisors and Windows Server operating systems, including patching, release upgrades, firmware, and BIOS updates.
• Serve as a subject matter expert for Windows, identity, virtualization, and automation platforms
  .
• Manage server and identity platform stability, security, performance, and capacity
  .
• Adapt, improve, develop, execute, and troubleshoot Windows provisioning and automation scripts
  , leveraging Power Shell and other scripting technologies to streamline deployments.
• Perform root cause analysis and drive long‑term remediation for supported environments.
• Deploy, maintain, and troubleshoot multiple virtualized environments (
  Development, Staging, and Production
  ).
• Implement and maintain Windows and identity security controls
  , including Bit Locker, LAPS, Credential Guard, Conditional Access, and Defender integrations.
• Develop and contribute to future strategy for identity, endpoint, server, container, and platform services
  , including providing budgetary input.
• Serve as a senior technical escalation point and mentor junior engineers
  .
• Prioritize multiple work streams simultaneously and meet deadlines in a fast‑paced environment.

• 7+ years of enterprise experience supporting Windows Server and Active Directory environments.
• Strong hands‑on experience with hybrid identity architectures
  , including Entra  (Azure AD) and Azure AD Connect / Cloud Sync.
• Proven experience supporting Microsoft Intune and modern Windows endpoint management.
• Advanced Power Shell scripting experience, including automation of identity, endpoint, and server workflows.
• Experience supporting Hyper‑V virtualization
  , including cluster implementation and automated failover.
• Strong troubleshooting skills with the ability to diagnose complex, cross‑platform issues.
• Ability to operate independently while collaborating effectively across infrastructure, security, and application teams.

• Experience working in security‑sensitive or regulated environments
  .
• Experience administering Microsoft 365 platforms.
• Familiarity with Solar Winds or similar monitoring solutions.
• Experience with Rubrik or comparable enterprise backup platforms.
• Experience with Tanium or other endpoint management / patching solutions.
• Linux experience and familiarity with Ansible, Puppet, Terraform or similar automation tools.
• Exposure to container platforms such as Red Hat Open Shift
  .

Sterling Trading Tech (Sterling)’s mission is to provide market‑leading, cloud‑based trading infrastructure, encompassing Trading Platforms, OMS, and Risk products to support both buy‑side and sell‑side firms. Sterling’s clients include clearing firms, broker dealers, proprietary trading groups, and hedge funds in over 20 countries. Sterling systems currently process over 10% of all U.S. matched equities.

Recently acquired by L Squared Capital Partners (L Squared), Sterling is entering a new phase of expansion and innovation. Sterling’s accelerated growth plans include additional staffing in both its product and sales organizations, new technology development and the release of incremental cloud services, with the addition of new asset classes and international coverage to drive global adoption of its offerings.

This is an exciting time to join Sterling’s growing team of trailblazers developing next‑generation trading technology in the fintech space.

Mid‑Senior level

Full‑time

Information Technology

Software Development

• Medical insurance
• Vision insurance
• 401(k)
• Paid maternity leave
• Paid paternity leave
• Disability insurance