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.
