Director Portfolio Execution Jobs (NOW HIRING)

Hi, we're Oscar. We're hiring a Manager, Portfolio Execution to join our Project Management 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 Manager, Portfolio Execution translates enterprise and market strategy into structured, executable programs that drive delivery across the filing lifecycle and broader growth portfolio. You will lead end-to-end program management for complex, cross-functional initiatives, ensuring strategic priorities are operationalized through disciplined governance, milestone management, dependency coordination, and execution oversight.

You will serve as a central connector across Product, Network, Regulatory, Operations, Technology, Compliance, and Market teams to drive alignment, accountability, and execution against critical business milestones. You'll maintain integrated timelines, identifying risks and dependencies, coordinating mitigation plans, and ensuring enterprise readiness for filings, market expansions, and operational launches.

You will report into the Senior Director, Project Management.

Work Location: This position is based in our New York office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $123,372 - $161,925 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Convert strategic business objectives into structured execution plans, integrated roadmaps, and scalable delivery programs.
• Lead end-to-end program management across the filing lifecycle, including planning, execution, readiness, and post-launch support.
• Drive execution of high-priority expansion initiatives, new market implementations, and enterprise growth programs.
• Ensure alignment across multiple concurrent workstreams while maintaining visibility into cross-functional impacts and dependencies.
• Establish and maintain integrated portfolio timelines, milestone tracking, and execution reporting.
• Coordinate enterprise-wide filing activities across Product, Network, Regulatory, Compliance, Operations, and Technology teams.
• Ensure critical filing deliverables are completed accurately and on schedule through proactive coordination and escalation management.
• Monitor filing readiness, identify execution risks, and drive mitigation strategies to protect regulatory and operational deadlines.
• Support governance and stage gate processes tied to filing readiness and downstream operational execution.
• Facilitate cross-functional working sessions, governance forums, and executive updates to drive decision-making and execution alignment.
• Partner with senior leaders to manage prioritization, resolve blockers, and ensure accountability across teams.
• Drive transparency through standardized reporting, RAID management, milestone tracking, and portfolio health assessments.
• Escalate risks, decisions, and resource constraints appropriately to leadership while proposing actionable mitigation strategies.
• Own integrated milestone management across interconnected workstreams and business functions.
• Identify upstream and downstream dependencies that may impact execution timelines or operational readiness.
• Maintain strong execution discipline by driving teams toward deadlines, decisions, and deliverable completion.
• Assess changes in scope, timelines, or strategic direction for downstream operational and regulatory impact.
• Support evolution of portfolio execution frameworks, governance standards, and operating models.
• Drive process improvements that enhance scalability, transparency, predictability, and execution quality.
• Contribute to development of tools, templates, and reporting mechanisms that strengthen portfolio oversight and execution management.
• Experience leading complex, cross-functional enterprise initiatives with multiple stakeholders and dependencies.
• Foster a culture of accountability, collaboration, and proactive problem-solving across teams.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• Bachelor's degree required; Master's degree preferred.
• 5+ years of experience in program management, portfolio management, strategic operations, consulting, or healthcare operations.

Bonus points:

• Healthcare payer, ACA marketplace, regulatory filing, or insurance operations experience.
• Experience supporting enterprise governance frameworks, stage gate processes, or PMO operations.
• Familiarity with portfolio management and collaboration tools such as Smartsheet, Jira, Monday.com, or similar platforms.
• Experience with regulatory, filing, operational readiness, or product implementation environments.

Travel required:

• If outside NY, 10%.