Jobs and Careers
OS

Senior Director, People Strategy

Oscar
New York City, United Statesfull_timeVerifiedPosted 2 Dec 2025
💰 $252,000/yr($192,000/yr$252,000/yr)

About the role

Hi, we're Oscar. We're hiring a Senior Director to join our People Strategy 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

You will play a critical and multifaceted role in establishing robust alignment between overarching business objectives and strategic People Priorities. This involves a deep understanding of the company's vision, its operational goals, and the human capital requirements needed to encourage a high performing culture. You will lead a team of HRBPs, providing guidance to lead talent management, organizational development, and employee engagement initiatives. You will help drive the talent strategy for the technology organization focused on organizational effectiveness, counseling and coaching talent and performance management, and ensuring an inclusive culture.

You will report to the Chief People Officer.

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 City 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: $192,000 - $252,000 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants, and annual performance bonuses.

Responsibilities

  • Partner with executive leadership and cross functional partners to set vision and build toward a best in class future state while serving as a single People strategy point of contact across the Insurance organization.
  • Lead initiatives to define our team's key objectives (alongside the business) and create frameworks for team members to set goals that align with those objectives and identify measurable results.
  • Drive the talent strategy agenda across multiple lines of business and keep the voice of the employee base in mind.
  • Provides guidance and input on business organization re-design, workforce planning and succession planning.
  • Partner closely with centers-of-excellence (e.g. Recruiting, Total Rewards, Talent Management, etc.). Meet on a recurring basis to understand needs, prioritize the employee enhancement, uncover opportunities for improvement.
  • Works closely with management and employees to improve work relationships, build morale, and increase productivity and retention.
  • Identifies training needs for business units and individual executive coaching needs.
  • Serve as an executive coach and mentor across the organization.
  • Lead a high performing People Strategy team supporting the technology organization.

Qualifications

  • 12+ years of experience in a People team function
  • 7+ years leadership experience with HRBP teams to successful outcomes
  • 5+ years analytical and problem solving skills

Bonus points

  • HealthTech, InsurTech, or Managed Care industry experience
  • Public company leadership experience
  • SHRM or related certifications

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.

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 re

Apply for this role

Generate a tailored application kit with a matched cover letter, interview prep, and CV highlights — in under 60 seconds.

Apply Now →Generate Application Kit

Free account required — sign up in 30s

Company

Oscar

View company profile →