Remote IT Senior Support Lead – Windows, M365 & Security

Sterlington, PLLC; Oregon; Hybrid; USD 70,000 - 110,000; Full time

Job summary

Sterlington PLLC is seeking an IT Senior Support Specialist to act as a trusted technical expert for a remote, distributed workforce. You will resolve complex issues, escalate where needed, and improve support delivery across the organization.

You’ll handle Microsoft 365, Windows, and macOS environments, manage device lifecycles, onboarding/offboarding, and contribute to knowledge resources and runbooks to reduce first‑contact resolutions.

Qualifications

• 5+ years of IT support experience.
• Strong working knowledge of Microsoft 365, Windows, and macOS.
• Experience handling escalated incidents and driving resolutions.

Responsibilities

• Serve as the escalation point for complex or high‑priority IT incidents and requests.
• Troubleshoot and resolve issues across Microsoft 365, Windows, macOS, Azure Virtual Desktop, user access, and remote connectivity.
• Lead major incident response with clear, calm communication to users and stakeholders.
• Manage endpoint lifecycle including provisioning, configuring, shipping, and maintaining laptops, mobile devices, and peripherals for a distributed workforce.
• Run onboarding and offboarding including account setup, access, and equipment.
• Administer Microsoft 365, Active Directory, and Entra ID day‑to‑day (users, groups, licensing, MFA, access requests).
• Support Intune operations: app deployment, patching, endpoint policies with Infrastructure support.
• Create and maintain knowledge base, runbooks, guides, and train support staff to resolve more issues at first contact.
• Track incidents, requests, and problems; monitor ticket trends to meet SLAs.
• Identify recurring issues, perform root cause analysis, and suggest permanent fixes.
• Look for automation opportunities and expand self‑service options, including AI tools.
• Support Security with access reviews, device compliance, phishing reports, and data protection practices.

Skills

Troubleshooting

Incident management

Communication

Tools

Microsoft 365

Windows

macOS

Azure Virtual Desktop

Active Directory

Entra ID

Intune

Job description

Sterlington PLLC is seeking an IT Senior Support Specialist to act as a trusted technical expert for a remote, distributed workforce. You will resolve complex issues, escalate where needed, and improve support delivery across the organization.

You’ll handle Microsoft 365, Windows, and macOS environments, manage device lifecycles, onboarding/offboarding, and contribute to knowledge resources and runbooks to reduce first‑contact resolutions.