NYC  SF        Events   Jobs   Deals  
    Sign in  
 
 
 

Oscar Health // health insurance
Apply To Job
 
 

 

Hi, we're Oscar. We're hiring an Associate Director to join our Benefits team.

Oscar is the first health insurance company built around a full stack technology platform & a focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselvesone that behaves like a doctor in the family.

About the role

You will play a pivotal role in the strategic design, implementation, & administration of Oscar's comprehensive employee benefits programs, including all health, welfare, retirement, & wellness initiatives. You will manage the annual Open Enrollment process from strategy to execution, ensure strict regulatory compliance (ERISA, ACA, etc.), & oversee vendor & broker relationships to maintain service excellence & cost efficiency. You will partner with Finance on budget management, leading & developing the Benefits & Leaves team, & supporting M&A activities. You will ensure our benefits are competitive, compliant, & aligned with our overall Total Rewards strategy.

You will report to the Senior Director, Total Rewards.

Work Location:

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

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

Pay Transparency:

The base pay for this role is: $144,000- $189,000 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, & annual performance bonuses.

Responsibilities

  • Contribute to the strategic plan & design while leading the implementation & administration of Oscar's benefits programs - including health, dental, life, disability, retirement plans, ancillary benefits, wellness programs, time away & leave offerings.
  • Monitor industry trends & benchmarks to effectively manage the annual review of the health & welfare program to achieve competitive market position while aligning with the overall Total Rewards Strategy.
  • Lead the execution of Annual Open Enrollment including aligning leadership on the renewal strategy, coordinating with the Workday team, setting the open enrollment calendar, employee communications, & the preparation of benefit educational materials & presentations.
  • Oversees the administration of the 401k plan & the 401k Committee- by working with the 401k administrator, financial planners, & auditors to ensure audit compliance with 401k plan & annual 5500 filings.
  • Manage relationships with benefit broker, carriers & third party vendors to ensure service levels & cost efficiency.
  • Collaborate closely with the Finance team to manage the benefits budget, ensuring alignment with overall company financial strategy & cost control goals.
  • Oversees the reconciliation, approval, & processing of monthly benefit invoices.
  • Ensure compliance with all federal, state & local regulations (e.g., ERISA, ACA, HIPAA, FMLA, COBRA) & the timely completion of regulatory reports & filings including 5500s & plan audits.
  • Curate & execute a wellness program to drive employee engagement that aligns with Oscar's Culture.
  • Lead & develop the Leaves & Benefits team.
  • Support M&A due diligence & integration activities related to benefits
  • Serve as an escalation point for complex employee benefit issues.
  • Compliance with all applicable laws & regulations
  • Other duties as assigned

Qualifications

  • 7+ years of benefits experience
  • Experience creating benefits offerings
  • Experience with Workday & Workday Benefits
  • Experience in owning vendor relationships
  • Experience presenting complex information across varying levels of seniority

Bonus points

  • Bachelor's degree or 4 years commensurate experience
  • HR certifications (i.e. SPHR, PHR, SHRM-SCP)
  • Experience creating wellness-based programming
  • Experience managing 5500 filings, 1094/95C, NDT & annual audit relative to 401K
  • Experience with mergers & acquisitions
  • Experience working in a fast paced environment

Travel

  • Up to 10%

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 & find both belonging & support. We're on a mission to change health care -- an experience made whole by our unique backgrounds & perspectives.

Pay Transparency:  Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, & 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 & disability insurance, & paid wellness time & reimbursements.

Reasonable Accommodation: Oscar applicants are considered solely based on their qualifications, without regard to applicants 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.

Artificial Intelligence (AI) Guidelines: Please see our AI Guidelines for the acceptable use of artificial intelligence during the interview process at Oscar.

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

 
 
 
 
 
About    Feedback    Press    Terms    Gary's Red Tie
 
© 2025 GarysGuide