Systems Administrator

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.

Location:

On-site in Los Angeles. This is an in-person role, not a remote position. Candidates must already live in, or be relocating to, the West Hollywood area and be able to work on-site at client offices on a regular basis.

About the role:

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, learn and advance quickly, be hyper reliable & responsible, 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 or San Francisco, with occasional remote support when those users are traveling. We’re looking to provide an above market compensation package for the highest level of technical skill, reliability, and service, so only candidates who are highly confident of their ability to provide white-glove service should apply.

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 in Los Angeles or San Francisco 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.

We are looking for someone with:

• A home base in Los Angeles and the ability to work in person at client sites. (This is not a remote role.)
• At least 7 years of IT experience, including 3+ years in a systems administration role, with evidence of growth.
• An advanced understanding of public and private AI/LLM platforms (e.g., ChatGPT Enterprise, Claude, Microsoft Copilot, Gemini, and self-hosted or private models), including how they handle data, identity, and access.
• Proven ability to deploy, configure, and support AI tools for users at scale, including SSO/SCIM provisioning, admin and data-governance settings, usage policies, and user enablement.
• Strong hands-on experience administering Microsoft 365 / Entra ID and/or Google Workspace (identity, licensing, email, and security policies).
• 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 (DHCP, DNS, VLANs, firewalls, Wi-Fi, VPN/zero-trust access).
• Familiarity with endpoint security, backup, and SSO/identity platforms (e.g., EDR tools, Okta).
• Working knowledge of bash and/or PowerShell scripting for automation.
• Exceptional customer service skills, including a clear communication style, very high reliability, and full ownership of all issues to complete resolution.
• Ownership and leadership character traits.
• Ticketing system organization and upkeep experience.
• The ability to be receptive and action-oriented in response to constructive feedback.
• A calm and focused demeanor in high-pressure situations.
• Strong professional and technical communication skills (both written and verbal).
• A passion for developing hard and soft skills and career advancement.
• Optional experience supporting audio/video systems (Crestron, Savant, etc.)

Compensation, benefits, and perks:

• Above-market base salary 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.