We are seeking a highly skilled and experienced Senior Systems Administrator to serve as the primary escalation resource and senior technical contributor within our IT team. This role is responsible for advanced troubleshooting, Microsoft 365 administration, security configuration, and root-cause analysis across cloud, endpoint, and infrastructure systems.

This individual will work closely with IT leadership to evaluate architectural improvements, provide technical recommendations, and execute approved changes. While IT leadership retains final authority on major technical decisions, this role is expected to operate with a high degree of autonomy and technical ownership in day-to-day operations.

The Senior Systems Administrator will serve as the escalation point for complex issues beyond Tier 1 and Tier 2 support while also contributing to strategic technical initiatives.

This role requires strong written and verbal communication skills and the ability to collaborate effectively across time zones.

Key Responsibilities

Microsoft 365 Administration & Architecture

Administer and optimize Microsoft 365 services including but not limited to:

Exchange Online
SharePoint Online
Microsoft Teams
Entra ID (Azure AD)
Microsoft Defender & Security tools

Implement and manage security policies, conditional access, and compliance controls
Recommend architectural improvements and best practices for approval
Execute configuration changes and platform enhancements
Monitor tenant health, security posture, and performance

Advanced Technical Support & Escalation

Serve as Tier 3 escalation point for complex technical issues
Perform deep root-cause analysis across:

Windows 10/11 endpoints
Identity and authentication systems
Microsoft 365 services

Troubleshoot persistent or recurring performance issues
Lead deep-dive troubleshooting efforts to identify systemic or environmental causes of issues that persist across hardware replacement or re-provisioning

Tier 1 & Tier 2 Coverage Support

Provide Tier 1 and Tier 2 end-user support when support technicians are unavailable or out of office
Assist with ticket backlog management during peak periods
Serve as a technical mentor and escalation resource for support technicians when they encounter complex or unfamiliar issues
Ensure continuity of service and timely resolution of user issues
Maintain a team-oriented approach to shared service delivery

Systems & Endpoint Management

Manage endpoint configuration and policies
Support device management platforms (e.g., Intune, Group Policy)
Diagnose OS-level issues, startup performance problems, and system conflicts
Maintain system documentation and technical standards

Technical Projects & Platform Initiatives

Lead and execute technical projects within the Microsoft 365 ecosystem and broader IT environment
Evaluate new technologies, platform changes, and service enhancements; provide technical analysis and recommendations to IT leadership
Plan and implement system migrations and service transitions
Manage configuration changes and feature rollouts that impact end users
Assess user impact and operational risk when introducing platform changes
Develop implementation plans including testing, communication support, and rollback strategies when appropriate
Ensure projects are completed with minimal business disruption and aligned to security and compliance standards
Document architecture decisions, configurations, and project outcomes
Participate in occasional AWS-related initiatives; prior AWS experience is beneficial but not required, as training will be provided

Security & Best Practices

Assist in strengthening Microsoft 365 security posture
Monitor and respond to security alerts
Participate in improving access control, MFA enforcement, and device compliance
Support vulnerability mitigation and system hardening efforts

Collaboration

Communicate technical concepts, issues, and solutions clearly and professionally to end users and internal stakeholders
Provide clear written documentation and status updates on ongoing issues and projects
Collaborate effectively with IT leadership across time zones
Partner with IT leadership on infrastructure planning
Provide technical guidance to support technicians
Contribute to process improvements and documentation
Balance reactive support responsibilities with proactive system improvement initiatives
Help elevate overall technical maturity of the IT team

Requirements

Required

5+ years of progressive IT systems administration experience
Deep hands-on experience administering Microsoft 365 (Exchange Online, SharePoint Online, Teams, Entra ID)
Strong understanding of Microsoft 365 security and compliance features
Advanced troubleshooting experience with Windows 10/11 endpoints
Experience performing root-cause analysis across identity, endpoint, and cloud systems
Ability to independently manage and execute technical projects

Preferred

Experience with Microsoft Intune or modern endpoint management
Experience supporting hybrid or cloud-first environments
Familiarity with AWS environments
PowerShell scripting experience
Relevant Microsoft certifications (MS-102, Security Administrator, etc.)

Benefits

HMO with 1 free dependent upon hire
Life Insurance
20 PTO credits annually
VL and SL cash conversion
Annual Performance-Based Merit Increases and Employee Recognition
Great Company Culture
Career Growth and Learning