Senior Systems Administrator

Chisholm Chisholm & Kilpatrick (CCK) is a private, public-interest law firm offering rewarding work with a focus on disabled military veterans and their families, as well as a wide range of other individuals who have been denied life, health, and disability benefits. As a team, we are committed to equality and inclusion in the workplace and seek to hire well-qualified and highly motivated individuals who best represent the diversity of our clients.

We’re hiring a Senior System Administrator to help maintain and evolve a modern hybrid infrastructure environment. This is a hands-on senior role with responsibility across Windows and Linux systems, Azure and Microsoft 365 services, endpoint management, backup and recovery, and day-to-day operational reliability. You’ll work closely with the IT Director, serve as a trusted escalation resource, and have meaningful ownership over the systems and services that keep the business running.

Core Responsibilities:

· Administer and support Windows Server, Linux, Azure, Microsoft 365, Active Directory, Entra ID, and Intune in a hybrid environment.

· Own patching, monitoring, backup and recovery processes, and operational documentation to help ensure system reliability and readiness.

· Serve as an escalation point for complex infrastructure, systems, and endpoint issues.

· Lead or support migrations, upgrades, and operational improvement initiatives across the environment.

· Contribute to disaster recovery readiness, security hygiene, and documentation supporting SOC 2 and NIST-aligned efforts.

· Partner with the IT Director on project planning, prioritization, and continuous improvement across the environment.

Requirements:

· 6+ years of systems administration, infrastructure, or senior technical support experience.

· Strong hands-on experience with Windows Server, Active Directory, Azure, Microsoft 365, and hybrid identity.

· Working knowledge of Linux administration and experience supporting cloud or hybrid infrastructure.

· Experience with Intune, endpoint management, and technical troubleshooting in a business environment.

· A collaborative, ownership-oriented working style with strong communication and sound operational judgment.

Additional Details:

• This role is a hybrid position requiring 3-4 days per week in our Providence, RI office.
• This is a full-time position
• CCK offers options for medical, dental, and vision insurance (including options for employer-paid medical insurance for the employee!) and other wellness benefits.
• Gym membership reimbursement
• 15 days of PTO (increasing over time) and 12 paid company holidays in 2026
• 401k matching
• Paid Parental Leave

For your application to be considered, please submit the following:

• Resume
• Cover Letter
• Later stages of the interview process include an assessment, internet speed test, and reference check.

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