IT Support Specialist

Title: Senior IT Support Specialist
Location: Remote → Onsite (Port Washington, WI)
Type: Contract-to-Hire (6 months → conversion based on performance)

Overview
We are hiring a highly capable IT Support Specialist to serve as a key IT presence for the region. This is not a traditional helpdesk role — it requires strong ownership, technical depth, and the ability to operate independently in a fast-paced environment.
You will be responsible for both delivering day-to-day IT support and improving how IT services are delivered. This role is best suited for someone who takes initiative, solves problems end-to-end, and continuously looks for ways to improve systems and processes.

Key Responsibilities
End-to-End IT Support Ownership
● Own and resolve 1st and 2nd line IT issues across hardware, software, and networking
● Act as the primary IT point of contact for the regional office
● Manage incidents and service requests through to resolution with accountability and clear communication

Operational Excellence & Continuous Improvement
● Identify recurring issues and implement long-term fixes to reduce ticket volume
● Improve onboarding and offboarding workflows through standardization and automation
● Maintain structured and up-to-date documentation for systems and processes

User & Device Lifecycle Management
● Provision and deprovision users across Active Directory, Entra ID (Azure AD), and Office 365
● Configure, deploy, and support Windows and macOS devices
● Manage device policies and compliance using Intune and/or Jamf

Cross-Functional Collaboration
● Partner with HR and internal teams to ensure seamless onboarding experiences
● Collaborate with global IT teams on escalations and standardization efforts
● Support executives and senior stakeholders with professionalism and urgency

Onsite IT & Infrastructure Support
● Support conferencing systems and office IT infrastructure
● Assist with IT setup for new or expanding sites (device deployment, vendor coordination)
● Troubleshoot basic networking and connectivity issues within office environments

What Success Looks Like (First 6 Months)
● Independently resolves the majority of IT issues with minimal escalation
● Reduces recurring tickets by addressing root causes
● Improves onboarding efficiency and consistency
● Establishes strong trust with regional stakeholders
● Brings structure, documentation, and clarity to IT processes

Required Experience
● 5+ years of IT support experience in a professional or enterprise environment
● Strong hands-on experience with:
○ Active Directory / Entra ID (Azure AD)
○ Office 365 (Exchange, Teams, SharePoint)
○ Endpoint management tools (Intune, Jamf, or similar)
● Experience supporting both remote and on-site users independently
● Experience with ITSM tools (ServiceNow, ManageEngine, or similar)
● Strong troubleshooting across hardware, Windows/macOS, and basic networking
● Familiarity with ITIL-based support environments

Preferred Experience
● Experience in high-availability or infrastructure-heavy environments
● Exposure to multi-site or distributed office support
● Experience supporting executive-level stakeholders
● ITIL certification

What We’re Looking For
● Strong ownership mindset — takes responsibility and follows through
● Proactive problem-solving — addresses root causes, not just symptoms
● Ability to operate independently with minimal oversight
● Clear and effective communication across all levels
● High accountability, responsiveness, and attention to detail

Compensation & Benefits
● Competitive compensation aligned to experience and market
● Conversion to full-time includes full benefits package

Why This Role
This role offers the opportunity to move beyond reactive IT support and take ownership of how IT operates in a real environment. You will have the autonomy to improve processes, solve meaningful problems, and directly impact the end-user experience.
● Work Model:
○ Start remote
○ Transition to full-time onsite (5 days/week)
● Travel: ~5–10% as needed