Winona, MN, United States · Sports Betting & Prediction Markets · Posted July 24, 2026
Key Responsibilities:
Provide first and second-level technical support to internal users via phone, email, chat, or in-person.
Provide on site support to our 4 WinCraft facilities in Winona, including but not limited to: desk-side support, printer troubleshooting, running network lines via a scissor lift, physically repairing or replacing tech hardware on the operation floor, and traveling between our 4 Winona sites to provide support.
Independently diagnose and resolve complex hardware, software, and network issues through systematic root cause analysis — without reliance on SOPs or step-by-step runbooks.
Document all support interactions, including the nature of the issue and the resolution steps taken, in our ticketing system.
Exhaustively investigate issues independently before escalating; when escalation is warranted, provide thorough documentation of steps taken, findings, and root cause analysis to appropriate internal teams or external vendors.
Manage and administer user accounts, mailboxes, and permissions across Active Directory, Azure Active Directory, and Microsoft Exchange Admin Center, including account creation, modification, termination, and group policy troubleshooting.
Write and execute PowerShell scripts to automate repetitive tasks, perform bulk user management operations, gather system diagnostics, and accelerate troubleshooting workflows.
Troubleshoot complex VPN, networking, mailbox, shared drive, and application access issues by leveraging available diagnostic tools and independent investigation rather than scripted procedures.
Assist with the setup, configuration, and maintenance of desktops, laptops, printers, and other peripheral throughout their usable lifecycles.
Collaborate with other IT teams to identify and implement process improvements and best practices.
Provide training and guidance to peers and users on basic IT procedures and best practices.
Take ownership and responsibility of an issue from start to a successful resolution.
Stay current with emerging technologies and trends in the IT industry.
Qualifications:
High school diploma or equivalent; Bachelor’s degree in Information Technology or related field preferred.
5 years of experience in a technical support role, preferably in a corporate environment.
Strong knowledge of Microsoft Windows and macOS operating systems, JAMF, Microsoft Office suite, Azure Active Directory, Microsoft Exchange Admin Center, and Microsoft Intune/Endpoint Manager.
Strong working knowledge of networking concepts, including TCP/IP, DNS, DHCP, VPN, and network troubleshooting methodologies; able to independently diagnose connectivity and routing issues without guided runbooks.
Hands-on experience administering Active Directory and Azure AD, including group policy management, conditional access, and user/device object management.
Experience supporting IT hardware in a warehouse environment, including but not limited to scales, thermal label printers, laser printers, barcode scanners, rf devices, tablets, and other warehouse tech.
IT certifications such as CompTIA A+, Network+, JAMF 100, or Microsoft certifications (e.g., MS-900, AZ-900, MD-102) are a plus.
Demonstrated ability to independently investigate and resolve technical issues through critical thinking and research — not by following step-by-step runbooks or SOPs. Must be comfortable formulating their own troubleshooting approach.
Works fully independently with minimal supervision; expected to self-direct research and resolution efforts on Tier 2 issues and take complete ownership without requiring managerial guidance on approach.
Ability to prioritize tasks and manage time effectively in a dynamic environment.
Strong interpersonal and communication skills, both verbal and written.
Proficient in PowerShell scripting; able to write scripts from scratch for user management, system diagnostics, and automation without relying on pre-built templates. PowerShell proficiency is strongly preferred.
Clearly documents client issue to ensure problem is clearly understood by others.
Can resolve more complex and critical issues without supervision and occasionally takes the lead on directing and resolving these issues.
Will document root cause and resolution of more complex issues to enhance overall knowledge level of team.
Actively works with team leader on developing and improving documentation and procedures.
Ability to lift up to 60 lbs, use ladders, comfortable working in a warehouse environment as needed, and comfortable with operating a scissor lift approx. 30ft in the air as needed. (Training provided)
Benefits
When determining base pay, as part of a final compensation package, we consider several factors such as location, experience, qualifications, and training.