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Helping you save time and money, by providing high quality, affordable health plans

Director, Operations - Cigna + Oscar

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Hi, we're Oscar. As you may have heard we are launching a new business line in partnership with Cigna! You can read about it here and here. We’re hiring an Operations Director to join our Cigna + Oscar Business 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.

About the role:

We’ve just announced a strategic partnership with Cigna to jointly provide commercial health insurance to small businesses in select markets. The two companies will begin offering the product under the Cigna + Oscar brand in late 2020. The new offering will bring together the depth of Cigna’s experience and provider relationships with Oscar’s high-touch, consumer-facing approach to customer service and care navigation. We’re committed to giving small business owners in these markets an affordable option that helps them and their employees save money and see the doctors they know and trust. Cigna + Oscar will make it easier for their employees to get appropriate care quickly and stay healthy.

You will be responsible for managing service readiness for Cigna + Oscar offering for all markets in 2020. You will serve as a counterpart to the Cigna + Oscar Launch & Expansion Lead and report into the SVP, Cigna + Oscar Business


  • Manage operational roadmap for getting Oscar ready to service for late 2020 enrollment date
  • Manage strategy, day-to-day, resourcing and prioritization for operations functions for Cigna + Oscar product line

    • Functions include Member and Provider Product, Concierge, Member & Provider Services, Clinical, Claims, Provider Data, Risk Adjustment, Eligibility & Billing, CG&A, Telemed, Pop Health, BH Ops & CM, Renewals, Compliance, Legal
  • Build strong relationships with key stakeholders at Oscar and Cigna and work effectively together

  • Own and manage Ops budget for the partnership


  • You have Bachelor’s Degree or higher
  • You have 7+ years of work experience in operational roles at renowned organizations with high quality bars
  • You have experience in and enjoy managing large projects that require strong organizational skills and collaborating with a broad array of different teams within an organization
  • You are a critical thinker who can distill complex concepts and regulatory requirements into easy to understand action items
  • You have acute attention to detail and always strive for perfection when writing formal documents.
  • You like building strong relationships with both internal and external stakeholders
  • You have passion for healthcare and a knack for making processes more systematic
  • You get things done, even if it’s crunch time

Bonus points:

  • Experience working in health insurance
  • Experience working specifically in the Small Group segment in health insurance
  • Experience in a tech/start-up environment

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 (accommodations@hioscar.com) 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.

Health insurance

Of course. Oscar employees get great health insurance for themselves and their families.


We want you to be able to save for a long retirement.

Unlimited pto

There's no limit to the number of vacation days you can take as a salaried employee. We work hard and encourage employees to recharge.

Fully stocked kitchens

Great coffee, healthy snacks, and catered lunches make it easy to stay energized at work.

Company social events

Monthly happy hours, outings, and an annual retreat create fun opportunities to connect with coworkers.

Volunteer with us

Join us for a variety of volunteer opportunities throughout the year.

Oscar Health at a glance

Helping you save time and money, by providing high quality, affordable health plans

Oscar Health focuses on Healthcare, Information Technology, Insurance, Technology, and Health and Insurance. Their company has offices in Los Angeles, New York City, New York, Dallas, and Tempe. They have a very large team that's between 1001-5000 employees. To date, Oscar Health has raised $1.268B of funding; their latest round was closed on August 2018 at a valuation of $3.6B.

You can view their website at http://hioscar.com or find them on Twitter, Facebook, and LinkedIn.

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