Lead IT Systems Analyst - Remote Position

About the Role

We are seeking a Lead IT Systems Analyst remote to join our dynamic team. This high-impact position is crucial for our IT operations, providing expert guidance across endpoint management, security compliance, and systems administration. As a Lead IT Systems Analyst remote, you will be the primary authority for complex IT issues, set technical standards, and mentor junior team members while owning critical initiatives and systems.

What You'll Do

• Serve as the primary escalation point for advanced hardware, software, and network issues, providing resolution guidance across Windows and macOS environments.
• Define and enforce technical standards, documentation, and best practices for IT support and system management.
• Lead user lifecycle management, including access provisioning, MFA, conditional access, and application assignments via Microsoft Entra ID (Azure AD).
• Manage software deployment, patching, OS updates, and hardware lifecycle, including procurement, tracking, and secure decommissioning.
• Administer Microsoft 365 platform governance, licensing optimization, and configuration standards.
• Support IT security and compliance efforts, including endpoint security controls, audit readiness, and SOC 2 or similar compliance frameworks.
• Identify and implement automation opportunities using PowerShell, Python, or Bash to streamline IT operations and improve efficiency.
• Lead or co-lead major IT projects and contribute technical insight to the IT roadmap, ensuring scalable and secure IT systems.

Requirements

• Bachelor’s degree in IT, Computer Science, or related field, or equivalent hands-on experience.
• 5-8 years of progressive IT systems experience with demonstrated technical ownership and leadership by expertise.
• Advanced knowledge of Windows and macOS administration, including OS-level troubleshooting and system management.
• Proficiency with Microsoft 365, Entra ID (Azure AD), Intune, and Jamf Pro.
• Solid understanding of IT security principles, endpoint security tools (EDR, DLP), and compliance processes (SOC 2 or similar).
• Experience with ITSM platforms such as Jira Service Management or ServiceNow.
• Strong scripting skills in PowerShell, Python, or Bash to automate processes and improve operational efficiency.
• Excellent collaboration and mentoring skills, with the ability to guide junior staff and influence cross-functional teams.
• Comfortable working autonomously in a remote-first environment and traveling occasionally for critical engagements.

Nice to Have

• Relevant certifications (CompTIA Security+, Microsoft 365 Endpoint Administrator, ITIL v4).
• RMM tool experience, cloud infrastructure familiarity, and networking fundamentals.

What We Offer

• Competitive compensation package, including potential equity or stock options.
• Flexible work schedule with a remote-first environment.
• Comprehensive healthcare, retirement plan match, and wellness programs.
• Unlimited paid time off and support for work-life balance.
• Opportunity to make a tangible impact on IT systems and organizational growth.
• Collaborative, distributed team environment with learning and mentorship opportunities.