Senior IT Engineer, Oscar Health
$149-195.6k
+ Company equity grants and annual performance bonuses
More information about location
3 days a week in office
Digital healthcare insurance
Be an early applicant
Digital healthcare insurance
1001+ employees
Be an early applicant
$149-195.6k
+ Company equity grants and annual performance bonuses
More information about location
3 days a week in office
1001+ employees
Company mission
To make a healthier life accessible and affordable for all.
Role
Who you are
- 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
Desirable
- 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
What the job involves
- 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
- 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
Our take
The US healthcare system is the world's largest and most expensive, but has health outcomes worse than other advanced economies. Oscar Health is focused on building a system of healthcare that is completely centered around its members' experience, offering direct-to-consumer insurance, with digital tools such as a virtual care experience forming a key part of the company’s business model.
Oscar is the first health insurance company built around a full stack technology platform. It gained a competitive edge by launching the "My Identity" functionality in 2021, that demonstrated a huge step for diversity and inclusion in healthcare, enabling users to input their names, pronouns and gender identity. It also provides access to health providers that will understand a user's language, race, ethnicity, and health situation, showcasing the company's focus on optimizing member experiences.
The company has secured good funding in the past, and expanded into new markets and states since its launch. This has fuelled growth and supported ventures such as its Culturally Competent Care Grant Program. An upcoming market expansion forms a key part of the company's plans to "more than double" membership by 2027.
Steph
Company Specialist at Welcome to the Jungle
Insights
-1% employee growth in 12 months
Company
Funding (last 2 of 9 rounds)
Dec 2020
$140m
LATE VC
Jun 2020
$225m
LATE VC
Total funding: $1.5bn
Company HQ
Hudson Square, New York, NY
Leadership
Mario Schlosser
(Co-Founder & President of Technology)Started their career at McKinsey where they were a Fellow Senior Associate. Founded Vostu where they held the Chief Scientist role before co-founding Oscar Health.
Mark Bertolini
(CEO)Previously Co-CEO at Bridgewater Associates, Chairman and CEO at Aetna as well as EVP at Cigna and Nylcare Health Plans.
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