L2 Technician – Microsoft 365 Focused

Working Schedule: Monday – Friday, Hawaiian Standard Time

Work Arrangement: Fully Remote

Salary: $1,700 - $2,000

Employer: MSP company operating in Hawaii, USA.

Job Summary

We are looking for an experienced Level 2 IT Technician with a strong Microsoft 365 focus to handle escalated and moderately complex technical issues across client environments. The ideal candidate has hands-on experience with Microsoft Entra ID, Exchange Online, SharePoint, OneDrive, Teams, Windows, identity, networking, and business applications.

What We're Looking For

A proactive L2 technician who takes ownership of issues, communicates clearly, can troubleshoot beyond standard SOPs, and is comfortable working across multiple systems while maintaining strong service and security standards.

Key Responsibilities

• Resolve escalated L2 technical issues across Windows, Microsoft 365, identity, applications, hardware, and networking.

• Administer and troubleshoot Microsoft 365, Entra ID, Exchange Online, SharePoint, OneDrive, and Teams.

• Troubleshoot authentication, MFA, permissions, mail flow, synchronization, licensing, and user-access issues.

• Perform approved user, group, mailbox, licensing, and configuration changes.

• Investigate issues using administrative portals, logs, diagnostic tools, and technical documentation.

• Identify recurring or systemic issues and implement permanent fixes within scope.

• Maintain accurate ticket notes, technical documentation, SOPs, and resolution details.

• Provide clear client communication and properly escalate high-risk or L3-level issues.

• Provide technical guidance and support to Level 1 technicians.

• Assist with Microsoft 365, endpoint, infrastructure, and other technical improvement initiatives.

Requirements

• 3+ years of IT support, help desk, systems administration, or related experience.

• Hands-on experience administering and troubleshooting Microsoft 365 environments.

• Experience with Entra ID, Exchange Online, SharePoint, OneDrive, Teams, and identity management.

• Strong understanding of MFA, authentication, permissions, Conditional Access, and security concepts.

• Working knowledge of DNS, DHCP, TCP/IP, VPNs, and basic network troubleshooting.

• Experience with ticketing, remote monitoring, endpoint management, and documentation platforms.

• Strong troubleshooting, analytical, organizational, and communication skills.

• Ability to independently manage escalated issues and identify root causes.

• Experience working in an MSP, multi-client, or fast-paced IT support environment is preferred.

• High school diploma or equivalent required; technical education or equivalent experience preferred.

Preferred Certifications

• Microsoft 365 Certified: Collaboration Communications Systems Engineer Associate

• Microsoft Certified: Security, Compliance, and Identity Fundamentals

• Microsoft Certified: Identity and Access Administrator Associate

• Other relevant Microsoft, CompTIA, or industry certifications are a plus.