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

VP, Talent Strategy

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Hi, we're Oscar! We are looking for a strong data driven and operations focused leader for the Vice President of Talent Strategy position on our People Team in the New York City 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 a great leader of Talent Strategy to help us do so.

The Role:

The Vice President of Talent Strategy will report into the Chief People Officer and will oversee the HR Business Partners, Employee Relations, D&I and Learning & Development. This person will own the long term strategy of the core people practices, including performance management, people/leadership development, talent management, succession planning and diversity & inclusion.

The VP of Talent Strategy will be chartered with building a world-class organization to help lead the company through its next phase of growth. With a mission of revolutionizing the way we, consumers, think about and have access to our healthcare, Oscar is at a critical point of opportunity and scale.

As an HR and people guru, you will navigate the complex issues of a maturing startup, championing a people-focused, data focused and solutions-oriented approach to ensure that our organization is a well-oiled machine. If you are a passionate, creative, data-driven leader who shares our desire to make Oscar an amazing place to work.


  • Design, implement and maintain the appropriate processes, tools, systems and training necessary to scale and support the function
  • Organizational Development: Partner with leaders to understand and anticipate hiring and development needs against the capabilities needed to deliver business objectives; prepare updated workforce plans and forecasts that support overall business goals. This person will manage a team HR Business Partners and will partner with them when it comes to planning
  • Performance Management & Development: Oversee how we access performance management and the development of leaders in addition to talent management and success planning
  • Vision and Strategy: Work with our Executive team to collaboratively set and execute on the long-term vision for all HR/People functions as well as the organization at large, consistently improving our effectiveness and helping us achieve our overall business goals; drive future organizational design and all change management initiatives to help maintain a high-performing, motivated, and impactful team
  • Values and Culture: Help establish our company values and ensure that all decisions, programs, and processes are aligned with our culture and core beliefs
  • Diversity & Inclusion: Work with our Head of D&I to build, strengthen and further define our diversity and inclusion strategy.

Who are you?:

We are looking for someone with experience and passion for People operations and culture!

Must-have qualifications and expertise include:

  • 10+ years of related experience in a high-growth and fast-paced setting with managerial responsibilities (ideally at a technology company)
  • You have a Bachelor’s degree and/or Masters in a relevant field and appropriate HR certifications
  • Knowledge and experience in organization development, employee relations, training and development and Diversity & Inclusion.
  • Proven ambassador of culture
  • You think strategically but also focus on tactical and operational issues
  • We’re scrappy, being ok with digging into the weeds
  • Deep understanding and respect for applicable employment laws
  • Experience managing complex employee relations situations, regardless of staff level
  • An eye for details with patience and persistence to work until it’s right

At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring practices. It means that we work to cultivate an environment where exceptional people can be their most authentic selves and find both belonging and support. We're on a mission to change healthcare -- an experience made whole by your unique background and perspectives.

*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's Pay Transparency Policy 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.