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