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Associate, Strategic Planning and Enablement

Hi, we're Oscar. We're hiring a Associate, Strategic Planning and Enablement to join our team.

Oscar is the first health insurance company built around a full stack technology platform and a focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role

You will work cross functionally with internal and external Oscar stakeholders and representing the needs and interests of the department in company wide initiatives. We ask that you have strategic thinking,  project management, and communication skills with an ability to work across disparate initiatives and various stakeholders at the same time. The Member Experience Strategy  team is redefining the healthcare journey by delivering a member experience that disrupts the industry. The work we drive ensures that every member feels valued, supported, and empowered.

You will report to the Senior Manager, Member Experience Strategy.

Work Location:

Oscar is a blended work culture where everyone, regardless of work type or location, feels connected to their teammates, our culture and our mission.

If you live within commutable distance to our New York City office (in Hudson Square), our Tempe office (off the 101 at University Dr), or our Los Angeles office (in Marina Del Rey), you will be expected to come into the office at least two days each week. Otherwise, this is a remote / work-from-home role.

You must reside in one of the following states: Alabama, Arizona, Arkansas, California, Colorado, Connecticut, Florida, Georgia, Illinois, Indiana, Iowa, Kansas, Kentucky, Maine, Maryland, Massachusetts, Michigan, Minnesota, Missouri, Nevada, New Hampshire, New Jersey, New Mexico, New York, North Carolina, Ohio, Oregon, Pennsylvania, Rhode Island, South Carolina, Tennessee, Texas, Utah, Vermont, Virginia, Washington, or Washington, D.C. Note, this list of states is subject to change. #LI-Remote

Pay Transparency:

The base pay for this role in the states of California, Connecticut, New Jersey, New York, and Washington is: $98,400 - $129,150 per year. The base pay for this role in all other locations is: $88,560 - $116,235 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities

  • Lead the end-to-end management of cross-functional implementations/projects, including project plan creation, stakeholder engagement, managing cross-functional relationships to drive collaboration, edge case mitigation, and on-time completion. 
  • Evaluate overall departmental performance by creating, gathering, analyzing and interpreting data and metrics as well as assisting in development of departmental metrics and implementation of mitigation strategies
  • Collaboratively works with all relevant internal and external stakeholder groups to formulate proactive implementation, communications, and program strategies for successful change management and risk mitigation initiatives 
  • Mentor team members and promotes colleagues’ growth and professional development
  • Compliance with all applicable laws and regulations 
  • Other duties as assigned 

Qualifications

  • 3+ years of experience in strategy/ operations/ program management
  • 2+ years of experience in leading end-to-end projects / programs, independently and within a team environment
  • Experience analyzing data and using metrics to drive improvements in programs 

Bonus Points

  • Experience / background in a fast-paced operations environment 
  • Healthcare experience (Health Insurance, Health Systems, or Healthcare Consulting) is a plus
  • Successfully executed enterprise-wide initiatives: defined project plans, coordinated resources, managed implementation activities, and developed all processes associated with program rollout and ongoing support
  • Experience in a member-facing role or a function focused on enhancing the overall member experience

This is an authentic Oscar Health job opportunity. Learn more about how you can safeguard yourself from recruitment fraud here

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.

Pay Transparency:  Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, and experience. Full-time employees are eligible for benefits including: medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.

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.

California Residents: For information about our collection, use, and disclosure of applicants’ personal information as well as applicants’ rights over their personal information, please see our Notice to Job Applicants.

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CEO of Oscar Health
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Mark Bertolini
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Average salary estimate

$108855 / YEARLY (est.)
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$88560K
$129150K

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What You Should Know About Associate, Strategic Planning and Enablement, Oscar Health

Hi, we're Oscar! We’re excited to announce an opening for an Associate, Strategic Planning and Enablement to join our dynamic team. At Oscar, we're not just some health insurance company; we’re pioneers in reimagining health insurance through a full-stack technology platform focused on our members' needs. Imagine being part of a team that's reshaping the healthcare experience to be more personal and supportive—this is the kind of company we envisioned when we started Oscar in 2012. In this role, you'll be collaborating effectively with both internal and external stakeholders to advocate for your department’s interests within company initiatives. This involves strategic thinking, effective project management, and stellar communication skills that help bridge various initiatives and teams. The Member Experience Strategy team is on a mission to craft a healthcare journey for our members that stands out in the industry. Your influence will help ensure every member feels cared for and empowered throughout their experience. You'll be reporting directly to the Senior Manager, Member Experience Strategy, and working in a culture where everyone, regardless of their work location, is closely connected to our mission, values, and each other. If you live within commutable distance to any of our offices in New York City, Tempe, or Los Angeles, expect to join us in-person twice a week; otherwise, this is a remote role that opens to various locations across the country. At Oscar, we're delighted to offer competitive salaries, unlimited vacation, and comprehensive benefits to help you thrive both professionally and personally.

Frequently Asked Questions (FAQs) for Associate, Strategic Planning and Enablement Role at Oscar Health
What are the core responsibilities of the Associate, Strategic Planning and Enablement at Oscar?

As an Associate, Strategic Planning and Enablement at Oscar, your core responsibilities include managing cross-functional projects from the ground up, leading stakeholder engagements, and ensuring that projects are executed on time. You will also be involved in developing and evaluating departmental performance metrics and implementing strategies for efficient risk management. This role is essential for shaping the member experience at Oscar and ensuring that all initiatives align with our overall company goals.

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What qualifications are required for the Associate, Strategic Planning and Enablement position at Oscar?

To be considered for the Associate, Strategic Planning and Enablement role at Oscar, candidates should ideally have at least 3 years of experience in strategy or operations, along with a minimum of 2 years in leading end-to-end projects. Strong analytical skills are necessary as you will often analyze metrics and data to drive improvements within our programs. Moreover, experience in healthcare or member-facing roles can give you an added advantage in this position.

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How does Oscar support the professional growth of an Associate, Strategic Planning and Enablement?

At Oscar, we believe in nurturing talent, which is why as an Associate, Strategic Planning and Enablement, you'll have opportunities to mentor team members and help them grow professionally. Oscar fosters an environment of continuous learning and development, providing resources and support that allow you to enhance your skills and advance in your career while enjoying the company's generous benefits like unlimited vacation and comprehensive health coverage.

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What does the work culture look like at Oscar for the Associate, Strategic Planning and Enablement role?

Oscar promotes a blended work culture where all employees, whether remote or in-office, feel a strong sense of connection. As an Associate, Strategic Planning and Enablement, you will immerse yourself in an environment that embraces diversity, collaboration, and innovation. The culture encourages open communication and values the unique perspectives of every team member, ensuring that everyone feels a sense of belonging.

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What tools or software should an Associate, Strategic Planning and Enablement at Oscar be familiar with?

An Associate, Strategic Planning, and Enablement at Oscar should be well-versed in project management tools and software that facilitate cross-functional collaboration. Familiarity with data analysis tools will also be vital, as you will need to interpret data and gather metrics to drive program improvements. Experience with CRM systems may be beneficial in supporting communication efforts across stakeholder groups.

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Common Interview Questions for Associate, Strategic Planning and Enablement
Can you describe your experience with managing cross-functional projects?

In answering this question, focus on specific examples from your previous roles where you've successfully led cross-functional teams. Highlight how you coordinated with different departments, the tools you used for project management, and any challenges you faced—along with how you navigated them. This showcases your readiness for the Associate, Strategic Planning and Enablement position at Oscar.

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How do you evaluate the success of a project?

When discussing project evaluation, emphasize the importance of defining clear KPIs and metrics beforehand. Explain how you collect and analyze data after project completion to understand its effectiveness and areas for improvement. This will show your analytical mindset, which is a key trait for an Associate, Strategic Planning and Enablement at Oscar.

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What strategies do you use to engage stakeholders in projects?

Engagement strategies could include regular updates, open forums for feedback, and collaborative sessions throughout the project lifecycle. Provide examples of how you've successfully aligned diverse stakeholder interests to reach project goals, which is essential in the role of Associate, Strategic Planning and Enablement.

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How do you handle conflicts among team members?

In answering this question, emphasize conflict resolution skills such as active listening, mediating discussions to uncover the root of the issue, and fostering a solution-oriented approach. This demonstrates your abilities in maintaining collaboration within cross-functional teams—an important aspect of the Associate, Strategic Planning and Enablement position.

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Can you share an experience where you had to use data to make decisions?

Share a situation where data analysis influenced a critical decision. Discuss the tools you used, the types of data you analyzed, and the outcome of your decision. This is particularly relevant for the Associate, Strategic Planning and Enablement role, as data-driven insights are pivotal to driving improvements.

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Why do you want to work for Oscar as an Associate, Strategic Planning and Enablement?

Your answer should reflect your alignment with Oscar’s mission to enhance the healthcare journey for members. Discuss how your values resonate with their focus on using technology to support and empower members. This helps the interviewers see that you are not only a fit for the role but also share in Oscar's vision.

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How would you approach creating a project plan for a new initiative?

In your response, articulate the steps you would take to develop a project plan, including defining objectives, identifying stakeholders, allocating resources, and setting timelines. Demonstrate an understanding of the necessary components of effective project management, which is critical for the Associate, Strategic Planning and Enablement role.

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Describe how you ensure compliance with regulations in your projects.

Compliance is vital in healthcare. Discuss your experience in reviewing regulatory guidelines, ensuring all teams are educated on compliance standards, and implementing checks to maintain adherence throughout the project lifecycle. This signals that you take compliance seriously, which is especially important for the Associate, Strategic Planning and Enablement position.

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What does an ideal member experience look like to you?

Share your vision of member experience, highlighting the need for personalization, support, and accessibility. This question allows you to express your understanding of Oscar's mission and your commitment to enhancing the healthcare experience for members, aligning directly with the Associate, Strategic Planning and Enablement role.

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How do you prioritize tasks when managing multiple projects?

Discuss your methods for prioritization, such as identifying urgent versus important tasks, using project management tools, and communicating with your team to align priorities. This illustrates your organized approach to handling the diverse responsibilities as an Associate, Strategic Planning and Enablement at Oscar.

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Oscar Health is an American health insurance company headquartered in New York City. Through telemedicine, healthcare-focused technology interfaces, and clear claims pricing systems, the company focuses on the health insurance market.

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Full-time, remote
DATE POSTED
March 13, 2025

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