Senior Systems Administrator- Cloud, Identity, and Automation

Bertram Capital Management • Foster City, CA

10d • $130,000 - $150,000 • Hybrid

About The Position

Bertram Capital is seeking a Senior Systems Administrator to support and modernize our internal technology environment across our Foster City, CA, and Denver, CO offices. This role is intended for an enterprise-scale administrator with experience in regulated environments, cloud identity, endpoint operations, automation, and applied AI. This is not a junior help desk role.

Requirements

• 5+ years of systems administration experience in environments supporting 500+ users.
• Strong hands-on experience with Azure / Entra ID and Microsoft 365 administration.
• Experience supporting multi-site organizations.
• Background working in regulated or compliance-driven environments (financial services preferred).
• Experience with endpoint management and remote administration tools.
• Ability to automate operational tasks using scripting, APIs, or AI tooling.
• Ability and willingness to travel periodically between Foster City, CA, and Broomfield, CO.
• Must be located near Foster City, CA, or Broomfield, CO.

Responsibilities

• Administer Microsoft Azure / Entra ID and Microsoft 365 across multiple office locations.
• Partner with the Cybersecurity Analyst, who owns MDM strategy and policy, to implement and operate endpoint tooling.
• Execute migration from legacy on-prem Active Directory to cloud-only authentication for Windows and macOS.
• Provide in-person and remote IT support at Foster City and Denver offices as needed.
• Use remote management tools to monitor, patch, and remediate endpoints.
• Automate deployment, remediation, and reporting workflows using scripting and AI-assisted tools.
• Support audits, access reviews, and compliance evidence collection.
• Provide escalation-level support for executives and critical business systems.
• Participate in an on-call rotation and respond to after-hours incidents.
• Continuously identify opportunities to reduce manual work through automation and orchestration.
• Apply automation-first and policy-driven approaches to system design and operations.
• Leverage AI-assisted workflows to improve deployment speed, remediation, and reporting.
• Challenge legacy processes and replace them with simpler, more scalable solutions.
• Use data and telemetry to guide operational decisions instead of intuition.

Benefits

• Comprehensive medical, dental, and vision benefits are provided at no cost to the employee.
• We offer a generous 401K match as well as a “take what you need” PTO policy.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 11-50 employees