Technical Lead (M365 Focus)

This is a remote position.

Job Title: Technical Lead (M365 Focus)

Work Type: 

• Remote/WFH
  

• Fulltime 
  

Working Hours: 8am-6pm EST 

Start Date: ASAP

JOB OVERVIEW:

The Technical Lead serves as a high‑tier technical resource within the Managed Services Service Desk team, providing expert‑level troubleshooting, advanced incident resolution, and guidance for complex technical challenges. This role acts as the primary escalation point for unresolved issues and ensures high‑quality service delivery, technical accuracy, and rapid restoration of service. This role reports to the Service Desk manager.

JOB ROLE & RESPONSIBILITIES: 

1. Technical Escalation & Expert Troubleshooting

• Serve as the final escalation point for complex or high‑severity technical issues requiring advanced troubleshooting expertise.
  

• Diagnose and resolve advanced issues across, networking, virtualization, and security platforms as well as Microsoft 365, Windows 11 and Windows Server operating systems.
  

• Provide real‑time support and guidance to Tier 1–3 analysts during high‑priority escalations.
  

• Perform deep‑dive technical analysis of recurring issues to identify patterns and implement permanent resolutions.
  

2. Proactive Alert Monitoring & Response

• Monitor security alerts across monitoring platforms.
  

• Triage alerts based on severity, business impact, and SLAs.
  

• Perform advanced troubleshooting behind recurring alerts.
  

3. Escalated Ticket Ownership

• Own and resolve Tier 3+ or escalated tickets from monitoring systems.
  

• Ensure escalated tickets contain complete documentation.
  

• Resolve issues within SLA expectations.
  

4. Operational Coordination for Alerts & Escalations

• Coordinate with service desk leadership to optimize workload distribution.
  

• Communicate with clients and stakeholders during alert‑identified risks or degradation.
  

• Perform end of shift handoff of ongoing issues that will span across work shifts
  

5. Technical Advisory & Best Practices

• Advise teams and clients on best practices.
  

• Collaborate on design and optimization initiatives.
  

• Stay current with industry trends to improve tools and standards.
  

6. Alert‑Driven Process Improvement

• Analyze alert patterns to identify systemic issues.
  

• Improve workflows and monitoring logic.
  

• Tune monitoring platforms to minimize “noise” and omit unimportant alerts.
  

• Maintain updated documentation for runbooks and procedures.
  

7. Coaching & Knowledge Transfer

• Mentor analysts on advanced troubleshooting skills.
  

• Support onboarding of new employees.
  

• Lead workshops and post‑incident reviews.
  

• Timely and thorough documentation of critical/high severity escalations.
  

8. Other responsibilities

• Based on alert activity and volume, other responsibilities will be assigned
  

• Process design and documentation
  

• Flexibility - a key to success for this role
  

JOB REQUIREMENTS:

• 5+ years of experience in IT support, systems administration, engineering, or security.
  

• Deep technical expertise across Microsoft 365, Windows Server, networking, virtualization, and cybersecurity.
  

• Strong problem‑solving and communication skills.
  

• Relevant certifications (CompTIA, Microsoft, Cisco, ITIL, etc.) are desired.
  

• Previous experience and skills desired related to:
  

• Cisco networking hardware
  

• Fortinet
  

• Threat Locker
  

• Microsoft Sentinel
  

• Halo ITSM
  

• N-Able monitoring
  

• Deep knowledge of:
  

• Microsoft Entra ID (Azure AD)
  

• Conditional Access policies
  

• MFA / SSPR authentication flows
  

• Cloud PC and Windows App access behavior
  

• Strong ability to interpret:
  

• Sign-in logs
  

• Token issuance failures
  

• Security alert context
  

• Operational Judgment
  

• Experience acting as a technical
  

• Ability to make sound decisions under time pressure
  

• Comfortable blocking changes that increase risk, even when resolution is urgent
  

• Communication
  

• Clear, decisive communication in team chats, escalation threads, and verbal communications
  

• Ability to explain why a change is or is not appropriate
  

• Confident interacting with senior engineers and leadership
  

• Success Criteria
  

• Rapid and accurate resolution of assigned issues.
  

• Mentoring other analysts and growing their technical capability.
  

• High service quality and reduced repeat issues.
  

• Improved support effectiveness and documentation completeness.