Senior IT Engineer
About The Position
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. 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.
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.
Benefits
- medical, dental, and vision benefits
- 11 paid holidays
- paid sick time
- paid parental leave
- 401(k) plan participation
- life and disability insurance
- paid wellness time and reimbursements
- participation in Oscar's unlimited vacation program
- company equity grants
- annual performance bonuses
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
