Senior IT Engineer

Oscar Health•Los Angeles, CA

1d•$149,040 - $195,615•Hybrid

About The Position

Oscar is seeking a Senior IT Engineer to join their Engineering Team. Oscar is a health insurance company that utilizes a full stack technology platform and focuses on member service. As a Senior IT Engineer, you will be the primary technical point of contact for the organization as new teams transition into Zendesk. You will manage complex infrastructure such as Okta, JAMF, and Google Workspace, ensuring seamless service delivery. Your role will involve leading the end-to-end onboarding lifecycle, automating support infrastructure into a hyper-efficient, self-service ecosystem that maintains strict healthcare data security standards.

Requirements

5+ years of IT engineering experience supporting large-scale enterprise environments.
3+ years of experience in enterprise-level Zendesk Administration and architecture.
Proven experience creating integrations within Zendesk for Identity and Access Management (IAM) tools such as Okta, IIQ, or homegrown solutions.
Ability to write scripts in Python or BASH for customized reporting, API interactions, and advanced workflows.
Demonstrated ability to lead discovery sessions and act as a consultant for internal stakeholders.

Nice To Haves

Workato Certifications or proficiency in no-code solutions like Okta Workflows.
Zendesk App Developer Certification.
JAMF 300/400 or Apple Certified Support Professional.
Experience integrating Zendesk with ETM platforms like Oomnitza.

Responsibilities

Lead cross-functional discovery sessions with incoming teams to define technical requirements and translate business needs into actionable project plans.
Manage and architect the full Zendesk stack (Support, Guide, Explore, Talk) for a multi-brand environment, optimizing AI-driven Answer Bots and self-service tools.
Design automated Joiner/Mover/Leaver (JML) workflows and hardware/software provisioning triggers, integrating Zendesk with Oomnitza or similar ETM platforms.
Design and deploy complex workflows using Zendesk triggers, automations, and third-party middleware to eliminate manual overhead.
Build and maintain bi-directional integrations between Zendesk and core enterprise tools including Slack, Okta, and Google Workspace.
Enforce platform security policies to ensure compliance with HIPAA, SOC2, and SOX regulations.
Serve as the senior-most escalation point for complex configuration, Liquid markup, or API issues.
Maintain a comprehensive library of technical documentation for custom automations and system architecture.