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Oscar Health // health insurance
Sales, Full Time    New York, New York    Posted: Friday, May 01, 2020
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Hi, we're Oscar. Were hiring a Medicare Advantage Sales Manager to join our Sales 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.

About the role:

The Medicare Advantage Captive Sales Manager will be responsible for the building, management & oversight of the MA Captive Sales Team & for the assessment, development & implementation of captive agent growth strategies for Oscars Medicare line of business. You will report into the Northeast Sales Director.

Responsibilities include but are not limited to effective recruitment, training & best practices, strategic thinking, assignment of territories, territory development, coaching & mentorship, & analyzing data, to achieve top performance from the MA Captive Field Sales Team within required regulatory guidelines. This sales leader will also be responsible for synthesizing external information & present findings to Sales Leadership.


  • Plan & manage team member activities to achieve enrollment goals for MAPD line of business to meet Oscars membership objectives, & developing & implementing captive sales plans.
  • Identify & develop relationships with individuals & organizations that influence the buying behavior of our target consumer (i.e., providers, regulators, faith-based organizations, community organizations, & associations, etc.) Understand the strengths & weaknesses of each organization & how it impacts the marketplace
  • Maintenance of adequate levels of production by measuring, tracking & reporting sales productivity in accordance with established goals. Identify & incorporate training & coaching opportunities for front line sales representatives to ensure quality & effectiveness.
  • Work collaboratively across multiple functions including marketing & sales operations on team training (benefits/operations/sales skills) & ensure the Sales Department utilizes best practices.
  • Review all sales allegations for the assigned sales team. Join in collaborative oversight of Agent/Broker Network sales channel strategy, alongside the Sales Relationship & Broker Support Manager.
  • Oversee CMS required annual training & certification program & ongoing training as well as assignment of required ride-alongs for Sales Representatives, annual/quarterly & corrective action ride-along.
  • Coach & manage performance in achieving quantitative & qualitative performance targets; regularly reviewing sales results/activities & provide feedback/coaching on opportunities for improvement
  • Manage day-to-day time & activities of assigned agents to ensure appropriate leading indicators of success & corresponding sales results
  • Monitor sales results, trends & hold representatives accountable for achieving targets
  • Partner with the Recruiting Manager to source & select candidates to ensure a continual pipeline & sufficient base of staff to meet assigned sales/membership growth targets
  • Organize involvement in formal & on-the-job training to ensure an accurate understanding of our product, compliance/policy requirements, sales processes, brand & value proposition messages & sales systems
  • Organize activities, leads & territories to ensure effective & efficient coordination across the territory
  • Act as a liaison between Captive agents & Oscar sales process owners to ensure agents are appropriately set up & supported across their lifecycle. This includes, contracting, licensing/appointment, certification, training, enrollment administration, commission payment, agent servicing, etc.


  • Undergraduate degree
  • 3+ years of experience at a health insurance carrier
  • Have a NY state Insurance License
  • Able to travel up to 80% of time within aligned sales market area
  • Willing/able to commute to the Bronx & Lower Hudson Valley
  • Medicare sales experience in the Bronx and/or Hudson Valley

Bonus points:

  • Sales/territory management experience
  • Proven relationships within market
  • Be focused, versatile, dependable, multi-task oriented, flexible, & positive
  • Adapt effectively to challenging situations
  • Well-developed skills in prioritizing, organization, decision making, time management, & verbal/written communication skills
  • Strong interpersonal skills resulting in exceptional rapport with stakeholders
  • Entrepreneurial spirit & competitive attitude
  • Combine patience, determination, & persistence to troubleshoot client issues
  • Dynamic, results-oriented problem solver

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 aim to make health care affordable & accessible for all, & apply this same vision to our perks & benefits, including: medical benefits, unlimited 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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