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IT Engineer II

HHi, we're Oscar. We're hiring an IT Engineer II to join our IT team.

Oscar is the first health insurance company built around a full stack technology platform and a 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 key member of the IT Engineering team, the IT Engineer II is responsible for supporting enterprise applications and providing innovative solutions to business challenges through automation. This role involves managing user devices, analyzing, installing, modifying, and supporting operating systems and enterprise software. The IT Engineer II will play a crucial role in ensuring the seamless integration and operation of IT systems within the organization.

You will report to the IT Engineering Manager.

Work Location:

Oscar is a blended work culture where everyone, regardless of work type or location, feels connected to their teammates, our culture and our mission. 

This is a hybrid role in our New York office. You will work part of the time in the office and part of the time remote / work-from-home. #LI-Hybrid

Pay Transparency:

The base pay for this role is: $119,200 - $156,450 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants, and annual performance bonuses.

Responsibilities

  • Handle Single Sign-On (SSO) of new applications with Okta and troubleshoot related issues.
  • support the Mac OS fleet using Jamf, ensuring optimal performance and security.
  • Develop and maintain comprehensive documentation for supported applications.
  • Oversee the complete lifecycle of user identities, including provisioning and deprovisioning.
  • Implement and maintain automated workflows for user onboarding and offboarding.
  • Build policies and scripts using vendor APIs for SaaS services such as Google Workspace, Slack, and Zendesk.
  • Provide operational support, including account management, workflow optimization, log analysis, troubleshooting, and performance enhancement.
  • Participate in an on-call schedule to provide emergency services and respond to issues as per monitoring and escalation protocols.
  • Ensure computer systems comply with organizational guidelines and standard operating procedures (SOPs).
  • Establish, configure, test, and maintain operating systems and SaaS applications.
  • Ensure rapid response to technical issues to minimize downtime and maintain productivity.
  • Compliance with all applicable laws and regulations
  • Other duties as assigned

Qualifications

  • 3+ years of IT experience, with at least 1 year in systems administration within a cloud-first, modern IT environment.
  • 2+ years of experience in a high-growth SaaS environment.
  • Proficiency in Okta identity and access management.
  • 2+ years of experience using Jamf to manage Mac OS

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

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.

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.

California Residents: For information about our collection, use, and disclosure of applicants’ personal information as well as applicants’ rights over their personal information, please see our Notice to Job Applicants.

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Average salary estimate

$137825 / YEARLY (est.)
min
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$119200K
$156450K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

What You Should Know About IT Engineer II, Oscar Health

Hey there! At Oscar, we're on the lookout for an IT Engineer II to join our dynamic IT team in New York City. Since our inception in 2012, Oscar has been committed to revolutionizing health insurance by leveraging cutting-edge technology and ensuring our members are always at the forefront of our decisions. As an IT Engineer II, you'll be a key player in managing enterprise applications and finding innovative solutions to streamline our operations through automation. You'll tackle exciting responsibilities such as supporting our Mac OS fleet via Jamf and managing user identities with Okta. Your analytical skills will come in handy as you troubleshoot operating systems and optimize workflows to enhance productivity. Plus, enjoy the flexibility of our hybrid work culture, where you can collaborate with your teammates both in the office and remotely. With competitive pay and enticing employee benefits, including an unlimited vacation program and equity grants, this is a fantastic opportunity for IT engineers looking to make a meaningful impact. Eager for a challenge that combines technical expertise with a mission to change healthcare for the better? Join us at Oscar and help shape the future of health insurance!

Frequently Asked Questions (FAQs) for IT Engineer II Role at Oscar Health
What are the key responsibilities of an IT Engineer II at Oscar?

As an IT Engineer II at Oscar, your key responsibilities include managing enterprise applications, supporting user devices, implementing Single Sign-On with Okta, and ensuring the seamless operation of IT systems. You will also develop documentation for applications, manage the lifecycle of user identities, and provide operational support to enhance performance.

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What are the qualifications needed to become an IT Engineer II at Oscar?

To qualify for the IT Engineer II position at Oscar, you should have at least 3 years of IT experience, with a minimum of 1 year in systems administration in a cloud-first environment. Experience in a high-growth SaaS setting and proficiency in Okta identity management and Jamf for Mac OS management are also essential.

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What does the work culture look like for an IT Engineer II at Oscar?

Oscar promotes a blended work culture, where teams maintain connections regardless of their work type or location. As an IT Engineer II, you'll enjoy the flexibility of working both in our New York office and from home, fostering collaboration while ensuring work-life balance.

Join Rise to see the full answer
What can an IT Engineer II at Oscar expect in terms of compensation?

The base pay for the IT Engineer II role at Oscar ranges from $119,200 to $156,450 per year, accompanied by comprehensive employee benefits, equity grants, and an unlimited vacation program, rewarding both your performance and commitment to the company.

Join Rise to see the full answer
How does Oscar support employee growth for an IT Engineer II?

At Oscar, we believe in cultivating a learning environment. As an IT Engineer II, you'll have access to ongoing training, career development opportunities, and participation in performance reviews, empowering you to continuously enhance your skills and advance your career.

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Common Interview Questions for IT Engineer II
Can you describe your experience with user identity management as an IT Engineer II?

When answering this question, highlight your familiarity with tools like Okta and share specific examples of how you have managed identity lifecycles, including provisioning and deprovisioning users effectively.

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How have you implemented automation in your previous IT roles?

Discuss automation tools and processes you've employed, such as workflow automation for user onboarding and offboarding, and the impact these efforts had on operational efficiency.

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What are some challenges you faced in supporting an OS fleet and how did you overcome them?

Share specific challenges related to supporting a Mac OS environment, such as troubleshooting common issues, and detail the steps you took to resolve these challenges successfully.

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How do you ensure compliance with organizational guidelines in IT?

Explain your understanding of compliance protocols and how you have adhered to standard operating procedures in previous roles, ensuring that IT systems meet organizational standards.

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How do you prioritize tasks and manage your workload as an IT Engineer II?

Discuss tools and techniques you use for effective task prioritization, such as using project management software or time-blocking strategies, ensuring you meet deadlines and support team objectives.

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What experience do you have with documenting technical processes?

Talk about your approach to creating comprehensive documentation for applications and processes in previous positions, emphasizing the importance of clear and accessible resources for team collaboration.

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Describe your experience with SaaS applications and managing vendor APIs.

Highlight your familiarity with popular SaaS applications like Google Workspace and Slack, and discuss how you've interacted with vendor APIs to build policies and scripts for optimizing service use.

Join Rise to see the full answer
What steps do you take to secure user devices in your role?

Emphasize your strategies for securing user devices, such as using management tools like Jamf, ensuring compliance with security policies, and addressing vulnerabilities proactively.

Join Rise to see the full answer
How do you respond to being on an on-call schedule for IT support?

Share your perspective on the importance of being proactive when on-call, your strategies for maintaining calm under pressure, and how you ensure a quick and efficient resolution to issues.

Join Rise to see the full answer

Oscar Health is an American health insurance company headquartered in New York City. Through telemedicine, healthcare-focused technology interfaces, and clear claims pricing systems, the company focuses on the health insurance market.

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Full-time, hybrid
DATE POSTED
March 23, 2025

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