Senior IT Engineer

Namely; New York (NY); Hybrid; USD 149,040 - 195,615; Full time

Benefits offered by this job

Medical benefits

Dental benefits

Vision benefits

11 paid holidays

Paid sick time

Parental leave

401(k) plan

Life and disability insurance

Wellness reimbursements

Job summary

Oscar is hiring a Senior IT Engineer to be the primary technical contact as teams transition to Zendesk. You will bridge infrastructure—Okta, JAMF, Google Workspace—and service delivery, leading onboarding and automation to scale securely.

The role is based in NYC with a hybrid schedule (3 in-office days/week). You will own end-to-end platform projects, maintain security standards, and mentor junior engineers while driving self-service initiatives.

Qualifications

• 5+ years of IT engineering experience in large-scale enterprise environments.
• 3+ years of Zendesk administration and architecture experience.
• Experience building integrations for Identity and Access Management (IAM) within Zendesk (Okta, IIQ, or similar).
• Ability to write scripts in Python or Bash for reports, APIs, and workflows.
• Proven ability to lead discovery sessions and act as a consultant to stakeholders.

Responsibilities

• Lead cross-functional discovery sessions to translate business needs into project plans.
• Architect and manage the Zendesk stack for a multi-brand environment, with AI-driven self-service tooling.
• Design automated Joiner/Mover/Leaver workflows and provisioning triggers; integrate Zendesk with ETM platforms.
• Develop complex Zendesk automations and workflows to reduce manual work.
• Build and maintain integrations between Zendesk and core tools such as Slack, Okta, and Google Workspace.
• Enforce security policies to ensure HIPAA, SOC2, and SOX compliance.
• Serve as senior escalation point for technical issues and mentoring.
• Maintain comprehensive technical documentation for automations and architecture.

Skills

IT engineering experience

Zendesk Administration

IAM integrations

Scripting (Python or Bash)

Project leadership

Tools

Zendesk

Oomnitza

Okta

JAMF

Google Workspace

Job description

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. #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.

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
• vision benefits
• 11 paid holidays
• paid sick time
• paid parental leave
• 401(k) plan participation
• life and disability insurance
• paid wellness time and reimbursements

Artificial Intelligence (AI)

Our AI Guidelines outline the acceptable use of artificial intelligence for candidates and detail how we use AI to support our recruiting efforts.

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 ([e-mail]) to make the need for an accommodation known.

California Residents

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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.