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Oscar Health // health insurance
New York City    Posted: Wednesday, September 30, 2020
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Hi, we're Oscar. Were hiring a Senior Counsel, Employee Benefits & Executive Compensation  to join our Legal team in our New York office. 

Oscar is a technology-driven, consumer-focused health insurance startup founded in 2012 & headquartered in New York City. Our goal is to make health insurance simple, transparent, & human. We need your help to do so.

As Senior Counsel, you will be a key member of the Legal team responsible for providing advice & counsel on employee benefits, executive compensation & other related employment matters. This position works closely with Oscars People team, as well as Oscars leadership team.

Oscar is a dynamic, exciting & fast paced environment. You should be comfortable in an ever changing environment as we continue to grow!



  • Provide advice on executive compensation including long-term incentive compensation; deferred compensation; employment, change in control, & severance agreements; & related issues under Internal Revenue Code Sections 280G & 409A.
  • Negotiate, structure & implement equity compensation plans, bonus plans, deferred compensation arrangements, & change of control agreements 
  • Counsel on executive compensation & employment law matters, in the context of mergers & acquisitions, financings, & other corporate transactions.
  • Advise & negotiate employment agreements, separation agreements, & noncompete agreements
  • Be a primary point of contact for the People team to support their strategy & objectives
  • Help to develop, implement & continually improve company & team processes & procedures with respect to employee benefits matters

 About you:

  • J.D. from an ABA accredited law school & at least 5-7 years of relevant experience at a top tier law firm and/or in-house
  • Experienced & sophisticated attorney, with experience in a variety of complex benefits & executive compensation matters
  • Excellent critical thinking & analytical abilities, particularly in developing conceptual understanding of new topics for yourself & others
  • Demonstrated ability to take ownership with strong work ethic & follow-through skills
  • Excellent communication & interpersonal skills, both oral & written, with a proven ability to build strong interpersonal relationships & work cross-functionally
  • Detail-oriented & dynamic team player who thrives in a fast-paced environment


 Bonus points if you have:

  • Experience working in the healthcare industry or insurance industry
  • Experience with startups

Life at Oscar: 

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.

We encourage our members to care for their whole selves, & we encourage our employees to do the same with comprehensive medical benefits, generous paid-time off, paid parental leave, retirement plans, company social events, stocked kitchens, wellness programs, & volunteer opportunities.

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 ( to make the need for an accommodation known.

Pay Transparency Policy:

Oscar ensures that you won't be discharged or discriminated against based on whether you've inquired about, discussed, or disclosed your pay. Read the full policy here.

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