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Senior Director, Markets Strategic Advisory & Intelligence

May 29, 2026

Hi, we're Oscar. We're hiring a Senior Director, Markets Strategic Advisory & Intelligence to join our Insurance Product Development team. Oscar is the first health insurance company built around a full stack technology platform and a relentless 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: The Senior Director, Markets Strategic Advisory & Intelligence leads market-specific strategy development across Oscar's service areas. You will own the enterprise market intelligence and strategic insight function that serves as the single source of truth for product strategy, portfolio design, market expansion, and investment decisions. You will own the development of integrated intelligence capabilities spanning consumer research, competitor intelligence, market analytics and performance insights to ensure data-driven decision-making across our product portfolio. Working cross-functionally across product, network, clinical, sales, growth, and market leadership, this leader develops actionable strategies related to market expansion (MSA and new geography), product positioning, portfolio optimization, and segment-specific opportunities. You will serve as a strategic advisor to executive and market level leadership, translating market insights and performance data into clear recommendations that support market-level decision-making. You will report into the Vice President, Insurance Product Innovation and Development. Work Location: This is a remote / work-from-home role. You must reside in one of the following states: Arizona, California, Colorado, Florida, Georgia, Illinois, Massachusetts, Michigan, Nevada, New Jersey, New York, North Carolina, Ohio, Pennsylvania, Texas, or Virginia. 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: $218,592.00- $286,902.00 per year. The base pay for this role in all other locations is:: $196,732- $258,211 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program company equity grants and annual performance bonuses. Responsibilities: <ul> <li>Market Strategy & Intelligence <ul> <li>Lead market-specific strategic advisory functions across our service areas</li> <li>Oversee market research, competitive intelligence, and performance analytics of product portfolio specific dynamics to clarify growth and optimization opportunities</li> <li>Develop market and product specific right to win strategies informed by competitive, regulatory, and consumer trends</li> <li>Translate complex analyses into executive-ready recommendations and strategic insights</li> </ul> Portfolio Strategy & Market Expansion <ul> <li>Lead portfolio performance assessments and identify remediation and growth opportunities</li> <li>Support recommendations related to product positioning, market alignment, and portfolio investments (vendors, network, partnerships)</li> <li>Oversee analyses supporting market expansion, strategic partnerships, and new product or growth opportunities</li> </ul> Strategic Leadership & Execution <ul> <li>Be a strategic advisor to executive and market leadership teams</li> <li>Lead cross-functional strategic programs and planning efforts</li> <li>Facilitate strategic planning sessions alongside corporate strategy and finance, overseeing development of executive presentations and strategic materials</li> </ul> Team Leadership <ul> <li>Lead strategy, intelligence, and analytics team members</li> <li>Build partnerships with product, finance, sales, clinical, network, actuarial, and market leadership</li> <li>Foster analytical rigor, collaboration, and disciplined decision-making</li> <li>Compliance with all applicable laws and regulations</li> <li>Other duties as assigned</li> </ul> </li> </ul> Requirements: <ul> <li>Bachelor's degree.</li> <li>12+ years experience in healthcare strategy, insurance product strategy, consulting, or strategic planning</li> <li>6+ years people leadership experience managing multi-level teams</li> <li>Expertise in ACA individual and small group QHP markets</li> <li>Background in market analytics, competitor intelligence, and business case development</li> </ul> Bonus points: <ul> <li>MBA, MHA, MPH or related advanced degree</li> <li>Experience in internal strategy or consulting functions</li> <li>Familiarity with ACA market dynamics and healthcare competitive landscapes</li> <li>Experience supporting market expansion and healthcare partnership strategies</li> <li>Willingness to drive to outcomes, work with large datasets and distill analyses into actionable business insights with a structured and systematic thought process</li> </ul><div class="content-conclusion">This is an authentic Oscar Health job opportunity. Learn more about how you can safeguard yourself from recruitment fraud<a href="http://hioscar.com/careers/recruitment-fraud-alert"> here</a>. 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. Artificial Intelligence (AI): Our <a href="http://hioscar.com/careers/ai-guidelines" target="_blank">AI Guidelines</a> outline the acceptable use of artificial intelligence for candidates and detail how we use AI to support our recruiting efforts. 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 <a href="https://www.hioscar.com/legal/privacy/">Privacy Policy</a>.</div>

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...