VP, People Strategy at Oscar

We are Oscar

Headquartered in New York City, Oscar is aiming to revolutionize health insurance. The Oscar team is focused on utilizing technology, design and data to humanize healthcare.

We are changing how health insurance works. We want to create a healthcare experience that’s intuitive and puts people, not cost or workflows, first. We’re using a consumer-focused and tech-driven approach to do so. This positions us uniquely in the space - and creates one of the biggest opportunities in healthcare.

We brought together leaders from top technology, service and healthcare companies to deliver on our promise and seize this opportunity. We all work side by side in a collaborative, energetic, and creative environment. The result: better people, better ideas, and better healthcare.

This person will report into the Chief People Officer and will own the core processes of the People team. Overseeing the work of the HR Business Partners, this person will own the long term strategy of the core people practices, including performance management, people/leadership development, talent management, succession planning, and compensation/leveling practices.

The role:

The VP of People 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. The VP of People has a unique opportunity to help shape and drive the Company’s culture as it navigates growth and expansion across the country. The VP of People will report to the Deena Gianoncelli, Chief People Officer.

As an HR and people guru, you will navigate the complex issues of hyper-growth startups, championing a people-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, this could be your dream job!


Building core people principals:

  • 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 2 HR Business Partners and will partner with them when it comes to planning.
  • Performance Management & Development: Build out and oversee how we access performance management and the development of leaders in addition to talent management and success planning. For someone who likes to build and see things through for the first time, this is an exciting opportunity for you!
  • 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
  • Compensation and Benefits: Partner with our finance team to analyze existing compensation packages and plan future comp across all functions; benchmark our current benefits offerings and strategize for additional benefits as we scale

Who are you?

We are looking for someone with experience and passion for People operations and culture! This person is a career HR generalist with a knack in Organizational Development.

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 compensation (salary, equity and benefits), organization development, employee relations, recruiting for technical roles, employer branding, and training and development
  • 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 and run into makeshift conference rooms with a smile
  • 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

Above all else:

  • Friendly, thoughtful, and kind.
  • Humility, maturity, and lack of ego.
  • Always a point of view and an open mind.
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