Systems Administrator

This role supports our Technical Operations team by managing and hardening on-premises and cloud server infrastructures, ensuring robust backup and disaster recovery, and delivering proactive system administration across multiple clients. You will work closely with service desk, engineering, and security teams while maintaining high compliance standards and delivering exceptional reliability in a fast-paced, mission-driven environment that runs on the Entrepreneurial Operating System (EOS).

What You’ll Do

• Own the reliability, security, and performance of client Windows Server, virtualization, and Active Directory / hybrid identity environments
• Administer Microsoft 365 (Commercial + GCC/GCC High) and enforce tenant security controls (MFA, Conditional Access, secure baselines)
• Execute and validate tenant hardening, migrations, identity sync projects, and mail cutovers with minimal business disruption
• Operate and continuously improve backup, disaster recovery, and business continuity readiness (Datto, DR testing, restore validation)

• Serve as the escalation owner for high-severity (P1/P2) incidents-drive triage, troubleshooting, stakeholder communication, and rapid MTTR *Produce clear incident documentation and post-incident remediation plans (RCA, corrective actions, prevention strategy)

• Own and enforce change-management standards, ensuring approvals, backout plans, and documentation are complete and audit-ready
• Partner with Service Desk, TAC, and Security teams to prioritize escalations and ensure consistent service delivery across TechOps
• Guide clients on modernization initiatives, cloud migration strategy, and security enhancements aligned to compliance frameworks
• Lead infrastructure improvement efforts including hardware refreshes, virtualization optimization, patching standards, and DR enhancements
• Maintain and continuously improve operational runbooks, SOPs, and knowledge base documentation in IT Glue, ensuring high adoption and accuracy
• Mentor junior technicians by setting expectations, providing coaching, and raising the team’s technical and documentation quality standards
• Knowledge in EOS System is a plus

• Relevant Microsoft certifications in Windows Server Hybrid Administration, Microsoft 365 Administration, and Azure Administration, with baseline security knowledge (e.g., SC-900, Security+, or equivalent)
• Proven experience supporting Microsoft 365 Commercial and GCC/GCC High environments, including Azure Government, identity integration, and regulated tenant operations
• Strong working knowledge of compliance-driven environments and frameworks such as FedRAMP, CMMC, DFARS, and ITAR, with a disciplined approach to documentation and change control
• Advanced hands-on capability in Windows Server administration (hardening, patching, identity services, and performance management)
• Experience supporting virtualization platforms (VMware and/or Hyper-V), including lifecycle management, optimization, and troubleshooting
• Strong PowerShell / automation skills, with the ability to streamline operational tasks and reduce repeat incidents through scripting and standardization
• Experience executing complex projects including server migrations, tenant hardening, identity sync/SSO implementation, and secure baseline deployment
• Demonstrated ability to lead through high-severity incidents (P1/P2), deliver clear technical documentation, and drive root cause remediation
• Value-add certifications such as VMware VCP, Veeam, Datto, or similar infrastructure/backup credentials (preferred)
• 3-7 years of Windows Server administration in production environments
• 3+ years supporting VMware/Hyper-V virtualization
• 2+ years administering Microsoft 365 environments (Commercial and/or GCC/GCC High)

Mindset We Value

• Owns reliability of systems and communicates status proactively.
• Performs effectively during high-severity incidents.
• Works seamlessly with service desk, engineering, and security teams; mentors junior technicians.
• Seeks certifications, automates repetitive tasks, & recommends process enhancements.
• Protects client data, enforces least-privilege access, and follows compliance procedures., Do you have at least 2 years of experience administering Microsoft 365 environments, including hands-on experience with regulated tenants like GCC (Government Community Cloud) or GCC High?* Are you a U.S. citizen or legal permanent resident capable of handling data subject to ITAR and DFARS compliance regulations?* Do you have at least 3 years of hands-on experience managing and hardening Windows Server environments and virtualization platforms (VMware or Hyper-V) in a production setting?* Do you have direct experience operating and validating enterprise backup and disaster recovery solutions (such as Datto, Veeam, or similar) including running regular restoration tests?*

• Competitive salary and commission eligibility.
• Flexible work environment
• Comprehensive health, dental, and vision insurance.
• 401(k) retirement plan with employer match.
• Company-paid life insurance and short/long-term disability coverage.
• Professional development and certification reimbursement.
• Collaborative team culture rooted in trust and humility.

Our commitment to equity, equal opportunity, inclusion, and diversity is part of our broader commitment to respecting fundamental human rights across our value chain. RSI Security is proud to be an Equal Opportunity Employer. The Company will consider for employment qualified applicants with arrest and conviction records. Share, Invitation for Job Applicants to Self-Identify as a U.S. Veteran

• A “disabled veteran” is one of the following:
• a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or
• a person who was discharged or released from active duty because of a service-connected disability.
• A “recently separated veteran” means any veteran during the three-year period beginning on the date of such veteran’s discharge or release from active duty in the U.S. military, ground, naval, or air service.
• An “active duty wartime or campaign badge veteran” means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.
• An “Armed forces service medal veteran” means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.

About Us: RSI Security is a leading cybersecurity compliance firm that specializes in providing comprehensive security assessment, advisory, and technical security testing services. We support organizations in navigating the complex cybersecurity landscape, ensuring they achieve and maintain compliance while managing risks effectively. About the Role A detail-driven, security-focused Systems Administrator to safeguard mission-critical client systems and ensure bulletproof backup integrity.