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.

• Administer and support Windows Server, Linux, Azure, Microsoft 365, Active Directory, Entra , 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.

• 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.

• 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

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