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 NYC 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.

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.

This is an authentic Oscar Health job opportunity. Learn more about how you can safeguard yourself from recruitment fraud

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At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring practices. It means that we cultivate an environment where people can be their most authentic selves and find both belonging and support. We're on a mission to change health care -- an experience made whole by our unique backgrounds and perspectives.

Pay Transparency

Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, and experience.

Full-time employees are eligible for benefits including: medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.

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Reasonable Accommodation

Oscar applicants are considered solely based on their qualifications, without regard to applicant’s disability or need for accommodation. Any Oscar applicant who requires reasonable accommodations during the application process should contact the Oscar Benefits Team (accommodations@hioscar.com) to make the need for an accommodation known.

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