Senior Systems Administrator

Trustwave helps businesses fight cybercrime, protect data and reduce security risk. With cloud and managed security services, integrated technologies and a team of security experts, ethical hackers and researchers, Trustwave enables businesses to transform the way they manage their information security and compliance programs. Trustwave delivers automated, efficient and cost-effective threat, vulnerability and compliance management. Trustwave is headquartered in Chicago, with customers in 96 countries. For more information about Trustwave, visit

Trustwave, a leader in cloud-based compliance and information security solutions, is looking for a Sr. Systems Administrator to work on the Infrastructure Team in Chicago. The Infrastructure Team is the division of IT that manages all internal systems and applications. The Senior Systems Administrator reports to the Infrastructure Team Manager.

The Sr. Systems Administrator will perform advanced, senior-level administration of enterprise class Server and infrastructure-based applications in a heavily virtualized environment.  The candidate will also be responsible for performing system software upgrades, including planning/scheduling, testing, change management, and performing production upgrades. Other responsibilities include, hardware planning and management, maintaining growth statistics, compute forecasts, software and hardware inventories, monitoring and maintaining continuity with system software licensing and maintenance agreements, and providing recommendations regarding hardware and system software planning and budgeting. This role works under minimal supervision with considerable flexibility for the use of initiative and independent judgement, and often acts as project leader for projects with limited duration.

Duties and Responsibilities:

  • Perform daily system monitoring, verifying the integrity and availability of all hardware, server resources, systems and key processes, reviewing system and application logs, and verifying completion of scheduled jobs such as backups.
  • Advanced Windows operating system and applications support.
  • Advanced Office 365 systems and application support
  • Advanced troubleshooting at the OS, application, and web services tiers.
  • Capacity to mentor and lead lower level engineers as needed.
  • Become subject matter expert in more than one environment within Trustwave’s critical corporate applications infrastructure.
  • Become thoroughly familiar with all compliance and security requirements as well as adhering to all corporate policies and standards.
  • Management of servers and application environments critical to business processing. This includes working with application teams responsible for hosted apps, performing application and OS updates as needed, and maintaining server security and compliance as required by corporate policy and standards.
  • Perform a variety of tasks and evaluation as it relates to VMware, maintenance of our current VMware environment and making sure it is optimally performing at all times.
  • Architect and design new virtual solutions to meet application needs.
  • Work closely with application teams on troubleshooting issues as well as planning requirements for new virtual servers that meet the application requirements.
  • Work with Network and Storage teams to create/support the virtual platforms – do we want to segregate “Storage” as a separate team?
  • Assist Application/Development teams with database performance related problems.
  • Work on making sure the environment is designed properly as well as proactively growing the environment to meet the needs of the business.
  • Builds and installs new systems and applications.
  • Perform regular security monitoring to identify any possible intrusions and work with internal compliance teams to remediate vulnerabilities as they arise.
  • Work with IT management on disaster recovery solutions for all systems and applications.
  • Analyze and recommend solutions to improve overall performance, redundancy and scalability of infrastructure.
  • Attend meetings and interact professionally with peers and management.
  • Troubleshoot and take ownership of issues that arise with various applications and systems and work to resolve them until a resolution is reached.
  • Work on projects assigned by manager and project management team.
  • Provide timely feedback to Managers on open issues and provide quick resolution.
  • Provide resolution of issues for postmortem review and analysis.
  • Help build solid productive relationships will all levels of leadership and support teams.
  • Facilitate effective and supportive team relationships to resolve operational and interdepartmental problems quickly.
  • Ability to build capacity and sustainability plans.
  • Ability to adapt to a fast-paced and evolving environment.
  • Passion for providing outstanding support of inbound incidents.
  • Excellent troubleshooting skills with a scientific approach to problem investigation and resolution including in-depth root cause analysis.
  • Work closely with OEM, break-fix and integration vendors during systems implementation and troubleshooting.
  • Perform research on new technologies and provide findings through verbal presentations and written reports.
  • Perform other project-related tasks as assigned by Manager on various initiatives.
  • Travel to data centers when required to resolve an issue or work on projects.
  • Participate in on-call rotation with other IT staff to support production and corporate sites.

Minimum requirements 

  • 5-10 years of hands-on experience or ability to demonstrate extensive expertise working in Windows server 2008 and 2012 system administration.
  • General administration experience with Linux, Red Hat Operating Systems.
  • 4 years hands-on experience administering VMWare (preferred Version 5.x/6.x).
  • Experience with VMWare vROps preferred.
  • Experience with Exchange online preferred.
  • Experience with Storage Area Network Engineering preferred.
  • Server hardware support experience in a heavy Dell environment preferred.
  • Experience with MS SQL and mySQL and storing, replicating and recovering databases.
  • MCSE, VMware VCP and Data Center Virtualization preferred.
  • Scripting experience (PowerShell, VBS, Bash, or shell scripts).
  • Excellent customer service skills.
  • Able to work and interact with others in a structured/team environment.
  • Accuracy and attention to detail, must have organizational skills.
  • Demonstrated documentation skills, Visio preferred.
  • Independent problem solver with troubleshooting, decision making and analytical skills.
  • Excellent verbal and written communication skills.
  • Demonstrated ability to communicate to nontechnical audience any technical issues.
  • Must be able to lift 20-40 lbs. of computer related equipment.
  • Must be able to travel locally, nationally or globally as needed.
  • Network Administration experience (Firewalls, F5 Load Balancers, LAN, DNS, etc.) a plus.
  • Data Center migration experience a plus.


We prefer college-educated applicants, but at minimum, high school diploma or equivalent is required for employment.

Trustwave is an Equal Opportunity Employer of Minorities, Females, Protected Veterans, and Individuals with Disabilities.

To All Agencies:

Please, no phone calls or emails to any employee of Trustwave outside of the Talent Acquisition team. Trustwave’s policy is to only accept resumes from agencies via the Trustwave Agency Portal. Agencies must have a valid fee agreement in place and they must have been assigned the specific requisition to which they submit resumes, by the Talent Acquisition team. Any resume submitted outside of this process will be deemed the sole property of Trustwave and in the event a candidate is submitted outside of this policy is hired, no fee or payment of any kind will be paid.

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