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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 Tempe, AZ 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.