Reports To: IT Infrastructure & Facilities Manager
Location: Milwaukee, WI (On-site)
Employment Type: Full-Time, Salaried, Exempt
About Wantable
At Wantable, we’re redefining retail through personalization. Our membership-based model and proprietary technology empower us to curate products that help customers discover confidence and joy through style.
As a data-driven fashion company, we combine human intuition with algorithmic intelligence to deliver personalized assortments – balancing creativity, analytics, and operational precision.
We're seeking a a hands-on IT Operations Lead to serve as a key operator in a lean IT team supporting ~275 employees across 4 locations. This is not a coordination role. This is a do-the-work, own-the-outcome role. You will be responsible for keeping day-to-day IT operations running smoothly, with a heavy focus on end-user support, ticket flow, and onsite execution, while also contributing to network and infrastructure support.
About The Role
This role requires someone who can independently drive execution and ensure IT operations run smoothly at all times.
This is a multi-functional role that combines hands-on helpdesk support with network and systems responsibility. You should be equally comfortable resolving day-to-day user issues and stepping into infrastructure or network troubleshooting when needed.
You will also coordinate with all IT team members to ensure consistent coverage and follow-through.
This role requires strong, hands-on expertise with Mac/Apple environments and Google Workspace, as these are core to how our business operates. If something breaks, slows down, or gets stuck, you own getting it fixed.
What You'll Do
End User Support Ownership (Primary Responsibility)
- Own the performance and outcomes of the helpdesk function from end to end
- Ensure tickets are prioritized, resolved quickly, and never sit idle
- Act as the escalation point for complex or unresolved issues and see them through to completion
- Provide hands-on support across Mac and Windows environments for hardware, software, and network issues
- Support onsite and remote employees with a high level of responsiveness and accountability
- Use AI tools to automate repetitive support tasks, improve troubleshooting speed, and enhance documentation
Onsite IT & Infrastructure Execution
- Serve as the primary onsite technical operator for hands-on IT work
- Handle device setup, troubleshooting, cabling, and physical network support
- Support switches, firewalls, VLANs, VPNs, and wireless networks
- Maintain MDF/IDF environments and ensure physical infrastructure is organized and reliable
- Proactively identify issues before they become problems
Systems, Access & Admin
- Manage user accounts, permissions, and security across Google Workspace and other platforms
- Support application setup, configuration, and troubleshooting
- Assist with onboarding and offboarding to ensure a clean, secure, and consistent experience
- Maintain accurate documentation and system records
Device & Asset Management
- Manage lifecycle of laptops, mobile devices, and accessories
- Own provisioning, deployment, and decommissioning of devices
- Manage MDM tools (ABM, Kandji, etc.) to ensure consistency and control
- Maintain accurate inventory and lifecycle tracking for all IT equipment
Collaboration & Communication Tools
- Support Google Workspace (Gmail, Drive, Meet) and Microsoft 365 tools
- Administer VOIP systems (e.g., RingCentral) including user setup and troubleshooting
- Support conferencing platforms such as Zoom and Google Meet
Vendors, Facilities & Coordination
- Act as the first responder for onsite IT and basic facilities-related issues
- Coordinate with vendors, building management, and service providers to ensure timely resolution
- Work closely with all IT team members to ensure seamless coverage and follow-through
Operational Ownership & Team Role
- Operate as a high-accountability, hands-on #2 in a lean IT function
- Help ensure IT operations run smoothly at all times, including stepping in to lead day-to-day execution when needed
- Drive consistency in how support is delivered across the team
- Take initiative, identify gaps, and fix problems without waiting to be told
Additional Functions
- Other duties as assigned. Duties, responsibilities and activities may change at any time with or without notice.
Requirements
What We're Looking For
- 3-5+ years of professional IT support or systems administration experience
- Strong troubleshooting and analytical skills
- Experience supporting Mac OS and/or Windows environments
- Familiarity with Google Workspace (Gmail, Drive, Admin Console)
- Basic understanding of networking (TCP/IP, VLANs, VPNs)
- Experience with helpdesk or Zendesk ticketing systems
- Excellent communication and customer service skills
- Highly organized with the ability to prioritize and multitask
- Self-motivated with a proactive, problem-solving mindset
- Comfortable using modern AI tools (e.g., ChatGPT, Claude, OpenAI) and assisting in the setup and support of AI-driven systems or devices (e.g., OpenCLAW)
Nice To Have
- Experience with MDM tools (Iru (Kandji), Action1)
- Experience with Endpoint security (SentinelOne)
- Experience with Network infrastructure (Ubiquiti, Cisco) or site surveys (Hamina)
- Experience with Cloud VOIP systems (RingCentral)
- Experience with Surveillance, Access control systems (Verkada)
- Exposure to virtualization, backup solutions
- Associate’s or Bachelor’s degree in IT, Computer Science, or related field
- Relevant certifications are a plus
Additional Requirements
- Must have a valid driver’s license and reliable transportation for onsite support and multi-location needs
- This role includes regular hands-on, onsite work and may require moving between locations as needed
- After-hours support or availability is expected, as this role is the first responder for emergency IT situations (e.g., outages, office changes, or new build-outs); will escalate to IT Infrastructure & Facilities Manager as second level escalation, when needed
- Ability to lift and move equipment (up to 40lbs ) and perform physical IT tasks (e.g., cabling, device setup, equipment installs)
You’ll Thrive Here If You:
- You don’t wait to be told what to do - you see gaps and move
- A collaborative team player with a “we can do this” attitude
- Adaptable and comfortable in a fast-growing, evolving environment
- Strong communicator who can work effectively with both technical and non-technical users
- Highly resourceful and proactive - able to identify, troubleshoot, and resolve issues without waiting for direction
- Comfortable operating with ownership and accountability in a lean, high-expectation environment
- You’re straightforward, practical, and focused on solving problems
How We Work At Wantable:
- High ownership. You are trusted to make decisions that directly impact customers and financial performance.
- Hard-working and hands-on. We move fast, stay scrappy, and focus on impact.
- Independent thinkers. We value leaders who confidently make data-driven decisions without layers of approvals.
- Low bureaucracy. We avoid committees, long processes, and unnecessary steps.
- Love of fashion & product. We combine data with intuition to create experiences customers love.
- Results over pedigree. What you’ve built matters more than where you’ve been.
Benefits
Why Wantable?
- Be part of a dynamic, fast-growing company that has innovation and creativity embedded in its DNA.
- A chance to shape our customers’ journey and leave a lasting impact on their self-confidence, one order at a time.
- Join a collaborative environment where your ideas matter, your efforts are rewarded and you can see results in real time.
We have a laid-back, casual environment in a state-of-the-art HQ in Walkers Point.
We offer flexible schedules, paid parental leave (mothers AND fathers), and a private room for nursing mothers.
Even more exciting: paid vacation and seven paid holidays per year, plus a 50% discount on all merchandise. You’ll be eligible for the discount on your first day.
Important, but maybe less thrilling: we have ample parking, we offer medical (traditional and high deductible), dental, and vision insurance, as well as a 401K (both pre-tax and Roth options).
