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Senior Data Scientist, AI Enablement

Oscar Health

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What enablement roles keep asking for: Stakeholder management (21%), SaaS (16%), Customer success (14%), Salesforce (14%) — counted across their open postings here.

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Oscar Health has 280 open roles listed here.

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Preparing for this interview

Interviews for enablement roles keep coming back to Stakeholder management, SaaS, Customer success, Salesforce. Practise those questions before you sit with Oscar Health.

Questions you are likely to be asked

  1. Why do you want to join Oscar Health?
  2. What is your experience with LLMs? Tell me one thing you learned the hard way.
  3. How would you explain your model's result to someone who is not technical?
  4. What would you check first if a model's accuracy dropped after going live?
  5. When would you not use machine learning for a problem?

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Hi, we're Oscar. We're hiring a Senior Data Scientist, AI Enablement to join our Data 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:

Oscar's data team is focused on pushing our understanding of the complex landscape of the healthcare and insurance business. Insurance companies sit on a trove of data that is both broad and deep—spanning financial claims, clinical medical records, and rich product interaction data from our members. 

As a Senior Data Scientist for AI Enablement, you will sit at the intersection of data science, data engineering, and artificial intelligence. You will be responsible for designing, building, and maintaining AI-powered analytical systems and pipelines that empower our internal stakeholders to self-serve their data needs. This is a builder-focused role: the ideal candidate is a data scientist with a strong engineering background (or vice versa) who is energized by turning ambiguous workflows into well-engineered, LLM-augmented data tools and automated insights.

You will act as a foundational driver for AI Enablement for Data. You will be expected to operate with a high degree of independence, taking projects from initial conception to launch. While you will own these workflows end-to-end, you won’t be building in a silo. This is a highly cross-functional position where you will partner closely with a talented group of AI engineers, software engineers, data scientists, and business stakeholders to bring scalable, production-ready solutions to life.

You will report into the Director, Data Science.

Work Location: This position is based in our New York City 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: $163,944 - $215,176.50 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants, and annual performance bonuses.

Responsibilities:

Requirements:

Bonus points:

This is an authentic Oscar Health job opportunity.

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.

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 (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 Privacy Policy.

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Listed on greenhouse · posted 2026-09-16. ApplySarthi collects openings and links to application pages; the role is advertised by Oscar Health, not by us.