Senior IT Engineer

Hi, we're Oscar. We're hiring a Senior IT Engineer to join our Engineering Team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

As a Senior IT Engineer, you will be the primary technical point of contact for the entire organization as new teams transition into Zendesk. You will bridge the gap between complex infrastructure—including Okta, JAMF, and Google Workspace—and seamless service delivery. You will lead the end-to-end onboarding lifecycle, transforming support infrastructure into a hyper-efficient, self-service ecosystem that scales through sophisticated automation and maintains strict healthcare data security standards.

Work Location: This position is based in our Los Angeles, CA office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $149,040.00 - $195,615.00 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program company equity grants and annual performance bonuses.

Responsibilities:

• Strategic Discovery & Consulting: Lead cross-functional discovery sessions with incoming teams to define technical requirements and translate business needs into actionable project plans.
• Platform Architecture: 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.
• Lifecycle Workflow Orchestration: Design automated Joiner/Mover/Leaver (JML) workflows and hardware/software provisioning triggers, integrating Zendesk with Oomnitza or similar ETM platforms.
• Advanced Automation: Design and deploy complex workflows using Zendesk triggers, automations, and third-party middleware to eliminate manual overhead.
• Integration Development: Build and maintain bi-directional integrations between Zendesk and core enterprise tools including Slack, Okta, and Google Workspace.
• Security & Compliance: Enforce platform security policies to ensure compliance with HIPAA, SOC2, and SOX regulations.
• Technical Escalation & Mentorship: Serve as the senior-most escalation point for complex configuration, Liquid markup, or API issues.
• Documentation: Maintain a comprehensive library of technical documentation for custom automations and system architecture.

Requirements:

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

Bonus points:

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