IT System Administrator

Job Summary

We are seeking an experienced IT System Administrator for a direct hire opportunity in San Juan, PR within the insurance industry. This role is ideal for a hands-on infrastructure professional who enjoys managing hybrid technology environments, supporting business-critical systems, and serving as a Level 2/3 escalation resource for complex technical issues.

This opportunity offers a stable, professional work environment with supportive leadership, collaborative teamwork, and meaningful infrastructure improvement projects. The IT System Administrator will contribute to system reliability, cybersecurity maturity, cloud and identity management, and long-term technology strategy while continuing to grow technical expertise in a business-critical IT role.

Key Responsibilities

- Administer Windows Server and Linux environments across physical, virtual, on-premise, and cloud infrastructure.
- Manage corporate networks, firewalls, VPNs, Wi-Fi, cloud platforms, and related infrastructure services.
- Administer Azure Entra ID, SSO, MFA, Conditional Access, Microsoft Intune, and mobile device management.
- Develop and maintain backup, disaster recovery, monitoring, patching, capacity planning, and infrastructure security processes.
- Provide Level 2/3 technical escalation, troubleshoot complex issues, and support infrastructure migrations and improvement projects.
- Automate administrative tasks using PowerShell, Bash, Python, and generative AI tools while maintaining documentation, runbooks, and procedures.

Compensation and Benefits

- Salary range: $50,000 to $60,000 per year.
- Job type: Direct hire.
- Location: San Juan, PR.

Required Qualifications and Skills

- Administer and support hybrid Windows Server, Linux, virtualized, network, and cloud infrastructure environments.
- Manage identity, access, endpoint, and security controls using Azure Entra ID, MFA, Conditional Access, and Microsoft Intune.
- Support backup, disaster recovery, patch management, infrastructure monitoring, scripting, and automation initiatives.
- Serve as a Level 2/3 escalation resource for complex infrastructure, systems, and network issues.

- Bachelor’s degree in Computer Science, Information Technology, or a related field.
- 3 to 4+ years of experience in systems administration, IT infrastructure, or networking.
- Advanced knowledge of Windows Server, Linux, networking, virtualization, cloud platforms, Azure Entra ID, and Intune.
- Experience with AWS, Azure, and/or Google Cloud environments.
- Experience with backup and disaster recovery planning, restoration testing, monitoring tools, patching, and system updates.
- Scripting and automation experience using PowerShell, Bash, Python, or similar tools.
- Knowledge of NIST Cybersecurity Framework 2.0 and cybersecurity best practices.
- Fluent in English and Spanish, both written and verbal.
- Strong troubleshooting, documentation, communication, vendor coordination, and cross-functional collaboration skills.

Preferred Qualifications

- Relevant certifications such as CCNA, CompTIA, Microsoft Azure, AWS, or equivalent.
- Experience supporting regulated industries such as insurance, financial services, healthcare, or other compliance-driven environments.
- Experience improving infrastructure standards, security controls, runbooks, and operational procedures.
- Familiarity with generative AI tools for IT automation, documentation, or operational efficiency.

Equal Opportunity Employer / Disabled / Protected Veterans

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For temporary assignments lasting 13 weeks or longer, AppleOne is pleased to offer major medical, dental, vision, 401k and any statutory sick pay where required.

We are committed to working with and providing reasonable accommodations to individuals with disabilities. If you need a reasonable accommodation for any part of the employment process, please contact your staffing representative who will reach out to our HR team.

AppleOne participates in the E-Verify program in certain locations as required by law. Learn more about the E-Verify program.

We also consider for employment qualified applicants regardless of criminal histories, consistent with legal requirements, including, if applicable, the City of Los Angeles’ Fair Chance Initiative for Hiring Ordinance. Pursuant to applicable state and municipal Fair Chance Laws and Ordinances, we will consider for employment-qualified applicants with arrest and conviction records, including, if applicable, the San Francisco Fair Chance Ordinance. For Los Angeles, CA applicants: Qualified applications with arrest or conviction records will be considered for employment in accordance with the Los Angeles County Fair Chance Ordinance for Employers and the California Fair Chance Act.