Oscar Insurance is hiring a

Senior Counsel, Employee Benefits and Executive Compensation

New York, United States

Hi, we're Oscar. We’re hiring a Senior Counsel, Employee Benefits and 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 and headquartered in New York City. Our goal is to make health insurance simple, transparent, and 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 and counsel on employee benefits, executive compensation and other related employment matters. This position works closely with Oscar’s People team, as well as Oscar’s leadership team.

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


 About you:

  • J.D. from an ABA accredited law school and at least 8+ years of relevant experience at a top tier law firm and/or in-house
  • Experienced and sophisticated attorney, with experience in a variety of complex benefits and executive compensation matters
  • Excellent critical thinking and analytical abilities, particularly in developing conceptual understanding of new topics for yourself and others
  • Demonstrated ability to take ownership with strong work ethic and follow-through skills
  • Excellent communication and interpersonal skills, both oral and written, with a proven ability to build strong interpersonal relationships and work cross-functionally
  • Detail-oriented and 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 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.

We encourage our members to care for their whole selves, and 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, and volunteer opportunities.

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 ([email protected]) 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.