About Trunk Club

Trunk Club (www.trunkclub.com) was started to solve a simple problem – shopping for clothes in stores or online just doesn’t work for most people. It’s overwhelming, inconvenient, and takes way too much time. With Trunk Club, men and women discover awesome clothes that are perfect for them without ever having to go shopping. We combine top brands, expert service, and unparalleled convenience to deliver a highly personalized experience that helps everyone look their best.

Our team is based in Chicago, IL and has grown to over 1,300 employees since starting out in December 2009. We have offices in Chicago, Dallas, DC, LA, NYC, Charleston, and Boston.

About the Team

We are a passionate, highly collaborative team using technology to innovate the shopping experience. Most of our technology stack lives in the cloud. We use AWS, Windows Server, VMWare, NGinx, Nagios, Jira/Confluence, Google Apps for Work, Fuze, Okta, SalesForce, and a host of other applications in pursuit of becoming a billion dollar company.

The Systems Engineer will be part of an agile team responsible for creating and maintaining a highly available environment to support a host of employee facing IT systems, services, and applications. The Systems Engineer will present recommendations and solutions based on business requirement. You will identify, recommend, and implement new technologies. The ideal candidate is eager, an excellent problem solver, and has strong passion for technology. You’ll be on a team participating in an on-call rotation, including 24/7 availability. The candidate will need to be productive in a fast paced environment and work with minimal supervision.

Our team is based in downtown Chicago, IL in the River North area. Are you interested?

What your background might look like:

• 5+ years experience administering core Microsoft product stack, including Server, Workstation, Active Directory, DNS, DFS, DHCP, and Group Policies
• 5+ years experience with identity and access management (IAM) experience with Active Directory, NTFS permissions, LDAP, and Single Sign On (SSO) solutions
• 5+ years administering desktop management tools in a mixed OS environment (JAMF / SCCM)
• Strong understanding of scripting (Powershell, Python, php) for job automation
• Proficiency using VMware VSphere and cloud management technologies
• Hands-on experience in storage, virtual storage, backup and disaster recovery.
• Solid understanding of networking (LAN, WAN, VPN, VLAN, Routing, Firewalls, etc.)
• Experience integrating and supporting REST APIs
• Experience with design, development, documentation, analysis, creation, testing or modification of computer systems.

Please DO NOT apply if:

• You'd feel like a fish out of water without a well-defined traditional corporate structure
• You're accustomed to using the phrase "it's not part of my job description"
• Coming into downtown Chicago is going to be challenging for you.

Please DO apply if:

• You're a process improvement junkie
• You approach projects and problems with a “Security First” mindset
• Configuring, patching, upgrading and performance tuning in Windows and VMWare environments is second nature.
• You enjoy automating simple repetitive tasks
• You can drive projects from beginning to completion
• You have the ability to document issues and resolutions with great detail
• You're a closer - not a manager, a coordinator, or an idea person - but someone who loves to get stuff done, and done well (done means in production)
• You are a “go-to” person because you're reliable, creative, resourceful, a good decision maker, and generally one of the most capable people amongst your peers
• You're articulate, persuasive, and a good listener
• Your friends and former employers would gush about you and your awesomeness