Systems Engineer, Windows

We are PEAK6, a leading investment firm. You'll find us headquartered in the historic Chicago Board of Trade building, where we first opened our doors in 1997. It's been over 20 years since we were one of the first firms to develop sophisticated proprietary technology to use in our trading business. Today, we continue to leverage our technical ingenuity and operational excellence across several investment areas, spanning early-to-mid stage growth capital, operational control, trading, and e-sports, while always proving value to the customer. Throughout the years, we've built and operated several financial technology firms, and we continue to evolve. You'll find a bit of everything here, and we're always looking to take on new endeavors.

As a Systems Engineer specializing in Microsoft Windows Technologies in Technology Experience, you will be instrumental in the experience of all our employees throughout the PEAK6 Family of Brands. We’re looking for someone who takes ownership of their work, is resourceful in their problem-solving skills and is able to think creatively. This individual will work together with a team to perform day to day management on all Microsoft Windows Technologies utilized within the organization. You are the subject matter expert for all things Microsoft Windows, workstation and server. You will take on projects that will require clear communication and completion in a timely manner. We want someone who has a passion for setting the performance bar and thrives in an energetic team environment, while delivering a fully integrated solution that fits into one unified technology stack.

You’ll be responsible for:

  • Providing onsite, phone, email, and chat support for end user Windows Operating System needs, workstation and server.
  • Collaborating with team members and leadership, implement great support processes, procedures, and documentation.
  • Identifying opportunities for business enablement through smart use of technology.
  • Developing, testing, and deploying scripts as needed to workstations and/or servers.
  • Managing and integrating multiple Active Directory environments.
  • Account Creation and automation.
  • Mentoring team members.
  • Managing, supporting and provisioning multiple Office 365 tenants.
  • Managing, supporting, and maintaining SCCM.
  • Writing clear, concise documentation for team members in wiki tools (Confluence).
  • Evaluating and recommending new software platforms and services.

You’ll gain loads of experience in this role but before you do, you should have:

  • 5+ years of experience working with Microsoft Systems Center Configuration Manager, specifically building and maintaining workstation images, application packages, and deploying software updates.
  • Extensive experience with Active Directory and PowerShell and developing/maintaining custom scripts.
  • Extensive experience with the Windows operating system, workstation and server.
  • Extensive Experience with Office365, including comprehensive knowledge of all applications and services within, including OneDrive and SharePoint.
  • Experience supporting TCP/IP networks and wireless networking.
  • Experience with a ticket-based support platform.
  • Experience in communication and collaboration technologies.
  • Excellent interpersonal communication skills.
  • An MCSA or MCTS in Systems Center or hold relevant deep experience with applicable platforms.


All of our engineers have these traits. You should, too.

Motivation       Collaboration               Curiosity

Integrity           Adaptability                 Ingenuity


Life at PEAK6

We want you to like coming to work so we work really hard to make your job fun and different from any other.


As a PEAK6 Systems Engineer, Windows, you can enjoy:

  • Generous medical, vision and dental plans
  • Matching 401(k) programs
  • Adoption assistance & family leave
  • Sabbatical program
  • Speakers Series
  • Massage days
  • Poker tournament with a grand prize of a World Series of Poker buy in
  • Sports leagues
  • Cornhole tournaments
  • Annual PEAK6 Party
  • Yoga classes
  • Tuition reimbursement
  • Lasik eye discount
  • Philanthropy events
  • Annual wellness screens and flu shots
  • Bagel Fridays/expiration lunches
  • Birthday gifts
  • Charitable matching gift program

Learn more about our culture on our website at


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