Happy Money is hiring a Senior Systems Administrator to support and modernize our internal technology environment across the Foster City, CA, and Denver, CO offices. This enterprise-scale role focuses on cloud identity, endpoint operations, automation, and applied AI.

What You'll Do

Administer Microsoft Azure / Entra ID and Microsoft 365 across multiple office locations.
Partner with the Cybersecurity Analyst 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.

What We're Looking For

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.
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.

Nice to Have

Experience in a financial services environment.

Technical Stack

Microsoft Azure, Entra ID, Microsoft 365
Active Directory
Endpoint management tools
Scripting, APIs
AI-assisted tooling

Team & Environment

You will partner directly with the Cybersecurity Analyst.

Benefits & Compensation

Total annual compensation: $130,000 - $150,000
Comprehensive medical, dental, and vision benefits provided at no cost to the employee.
Generous 401K match.
"Take what you need" PTO policy.

Work Mode

This is a hybrid role based in Foster City, CA and Broomfield, Colorado.

Happy Money values and celebrates many perspectives from a variety of cultures, genders, religions, national origins, ages, abilities, socioeconomic status, and sexual orientation. Our commitment to Diversity, Equity and Inclusion (DEI) ensures we are a place that attracts, grows, and promotes top talent from all backgrounds.