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Senior Manager, Portfolio Strategy & Business Cycle Execution

June 6, 2026

Hi, we're Oscar. We're hiring a Senior Manager, Portfolio Strategy & Business Cycle Execution to join our Strategy and Operations 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 Manager, Portfolio Strategy & Business Cycle Execution drives the end-to-end orchestration of portfolio strategy within the enterprise business cycle for multiple markets. You'll ensure that you define, sequence, and finalize strategic decisions on time, enabling successful annual regulatory filings and downstream operational execution (e.g., OE and 1/1 readiness). You will serve as the central integrator between strategy and execution, providing visibility, structure, and governance across portfolio planning, decision-making, and cross-functional dependencies. You will report into the Senior Director, Project Management. Work Location: This is a remote position, open to candidates who reside in: Dallas, Texas. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote Pay Transparency: The base pay for this role is: $134,136 - $176,053 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonus. Responsibilities: <ul> <li>Own the portfolio strategy intake and intake governance process, capturing, vetting, and aligning all initiatives to enterprise priorities.</li> <li>Maintain the single source of truth for portfolio strategy, including initiative scope, status, and ownership</li> <li>Lead portfolio planning and prioritization in partnership with local markets and cross-functional business partners, balancing enterprise goals, regulatory requirements, and capacity constraints</li> <li>Develop and manage the portfolio roadmap, ensuring alignment to filing timelines and broader enterprise milestones</li> <li>Establish and manage the decision calendar, ensuring you sequence and complete all critical strategy decisions on time.</li> <li>Drive on-time decision-making by partnering with leadership and escalating risks to timelines or clarity</li> <li>Ensure alignment of all strategy decisions to regulatory filing timelines, enterprise planning cycles, and downstream execution milestones</li> <li>Embed governance through stage gates and leadership forums to close decisions upstream and reduce downstream disruption</li> <li>Identify, track, manage and escalate cross-functional dependencies between strategy, filings, and operational execution</li> <li>Ensure downstream teams (Product, Network, Finance, Tech, Ops, Compliance, etc.) have clear, timely inputs to execute</li> <li>Proactively mitigate risks related to late decisions, fragmented inputs, or misaligned timelines</li> <li>Partner with execution teams to ensure strategy is actionable, sequenced, and implementation-ready</li> <li>Facilitate feasibility assessments for new initiatives, evaluating operational, technical, and regulatory complexity</li> <li>Partner with cross-functional teams to define what it takes to implement (resourcing, systems, timelines, risks)</li> <li>Ensure strategic initiatives are grounded in realistic execution plans and constraints</li> <li>Support trade-off decisions by providing clear visibility into effort, dependencies, and impact</li> <li>Own and continuously refine the intake and prioritization framework</li> <li>Drive clarity on what gets worked, when, and why, ensuring alignment to enterprise strategy and capacity</li> <li>Maintain and communicate roadmap updates, trade-offs, and changes to stakeholders</li> <li>Ensure transparency across leadership on portfolio progress, risks, and decision status</li> <li>Compliance with all applicable laws and regulations</li> <li>Other duties as assigned</li> </ul> Requirements: <ul> <li>6+ years of experience in program management, portfolio management, or strategy operations, preferably in a complex, cross-functional environment</li> <li>Experience managing large-scale, interdependent initiatives tied to critical timelines (e.g., regulatory, product launches, or enterprise transformations)</li> <li>Strong experience in governance, roadmap planning, and executive-level communication</li> <li>Demonstrated ability to drive decision-making and influence senior stakeholders</li> <li>Experience with dependency management across Product, Technology, Operations, and Compliance</li> <li>Strong analytical and problem-solving skills with the ability to translate strategy into execution</li> </ul> Core Competencies <ul> <li>Strategic Orchestration – Connects strategy to execution across a complex portfolio</li> <li>Decision Discipline – Drives clarity, accountability, and timeliness in decision-making</li> <li>Systems Thinking – Understands upstream/downstream impacts and interdependencies</li> <li>Execution Rigor – Brings structure, governance, and predictability to delivery</li> <li>Influence & Communication – Effectively engages stakeholders at all levels</li> </ul> Bonus points: <ul> <li>Experience working within a rapidly scaling organization</li> <li>BA/BS Degree</li> <li>Masters in Business Administration or healthcare related field(s) preferred</li> </ul> Travel required: • If outside NY, 10%.<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...