Systems Administrator

We’re looking for a Systems Administrator who can use their technical depth and customer service skills to keep our clients’ environments secure, stable, and running at their best and play a key role in our company’s growth. The majority of this role is hands-on systems administration: managing identity, endpoints, email, networks, and security tooling across our client base, and leading improvement projects from start to finish. A growing part of that work is AI: we’re helping clients adopt public and private AI/LLM tools safely, and this role will be central to deploying, securing, and supporting those tools for users at scale. You’ll work on-site with clients and their VIP users in Los Angeles, with occasional remote support when those users are traveling.

Some responsibilities include:

• Administering, maintaining, and securing client systems, including identity, email, endpoints, and network infrastructure.
• Deploying, administering, and supporting public and private AI/LLM platforms across client organizations, from pilot through company-wide rollout.
• Configuring AI tool security and governance (SSO, provisioning, data retention, connector and integration permissions) in line with client policies.
• Training and enabling users on AI tools, building documentation and best practices, and serving as the go-to resource for AI questions and troubleshooting.
• Managing user lifecycle (onboarding and offboarding), access, and permissions across client environments.
• Deploying and maintaining device management, patching, backup, and security tooling across Mac and Windows fleets.
• Planning and executing state of the art technical improvement projects (migrations, rollouts, and infrastructure upgrades) for clients.
• Working on-site at client offices and directly with client VIPs to tackle a diverse range of challenges.
• Providing escalation-level technical support in person, by phone, email, and chat, including occasional remote support for VIPs while traveling.
• Being available, flexible, and on-call for periodic after-hours and/or weekend work, including maintenance windows.
• Being able to work with a team to solve difficult problems.
• Creating and maintaining technical documentation, runbooks, and system configuration records.

• A home base in Los Angeles or West Hollywood, or willingness to relocate to the West Hollywood area, and the ability to work in person at client sites. (This is not a remote role.)
• Eligibility to work in the United States.
• At least 7 years of IT experience, including 3+ years in a systems administration role, with evidence of growth.
• Experience deploying, configuring, and supporting AI tools for users at scale, including SSO/SCIM provisioning, admin and data-governance settings, usage policies, and user enablement, is a plus.
• Strong hands-on experience administering Microsoft 365 / Entra ID and/or Google Workspace.
• Demonstrable experience administering and supporting Mac OS environments. Windows experience is a plus.
• Experience with Jamf Pro or other MDM platforms, including configuration profiles, policies, and patch management.
• Solid networking knowledge.
• Familiarity with endpoint security and SSO/identity platforms (e.g., EDR tools, Okta); familiarity with backup platforms is a plus.
• Working knowledge of bash and/or PowerShell scripting for automation is a plus.
• Exceptional customer service skills, including a clear communication style, very high reliability, and full ownership of all issues to complete resolution.
• Availability for periodic after-hours or weekend on-call work, including maintenance windows.
• Optional experience supporting audio/video systems (Crestron, Savant, etc.)

• Above-market base salary of $140,000-$160,000 annually for excellent technical and communication skills.
• 95% coverage for medical/dental/vision premiums and more.
• 401k with employer match.
• $125 monthly technology reimbursement.
• $150 monthly meal stipend.
• $100 healthy living expense program.
• Generous reimbursement and bonuses for learning and training, including technical certifications.
• Flexible working hours.
• Generous PTO, sick and family leave policies.

At Cascade, we have committed ourselves to being a diverse and inclusive workplace, ensuring our employees are comfortable bringing their authentic selves to work every day. We value unique perspectives and believe this is critical to solving complex problems. Everyone is welcome and encouraged to apply.

Cascade is a rapidly-growing MSP (managed service provider), offering tech services in New York, the Bay Area, Los Angeles, and beyond. We provide a world-class service to high-end clients in the Financial Services industry.