Associate, Strategic Finance

About the role

The Associate, Strategic Finance serves as a key financial partner responsible for owning the narrative of corporate strategy through rigorous analysis and clear communication. You will translate the vision of executive leadership into concrete, actionable plans while providing sharp, data-driven insight to guide critical business decisions. This role is central to driving business reviews, shaping full-year financial forecasts, and delivering analytical support that influences strategic direction at multiple levels. You will challenge existing assumptions by interrogating data, which directly informs pricing strategies and portfolio choices aimed at protecting healthy margins and fostering sustainable growth. The position requires synthesizing complex information into compelling recommendations that combine a data-driven methodology with strong business intuition tailored for senior executive audiences.

You will report directly into the Senior Director, Strategic Finance & Corporate Development, functioning as a critical extension of their strategic oversight and analytical capacity. The role demands close collaboration with Finance leaders across the organization, working hand-in-hand on business reviews, full-year planning cycles, and establishing a true strategic partnership with business leadership to align financial planning with operational realities. A core responsibility involves creating new reporting frameworks and analytical insights designed to ensure deep visibility into business spending patterns, variance analysis, and forward-looking projections. Findings derived from this analysis are presented to multiple levels of leadership, from senior managers to executive stakeholders, to facilitate informed decision-making. As business priorities evolve, you will also absorb additional duties and shifting scope to ensure the finance team remains agile and responsive.

Work location and schedule

This position is based in the New York City office, requiring a hybrid work schedule that specifies three days of in-office work per week to maintain team cohesion and collaboration. Thursdays are designated as a required in-office day to facilitate essential team meetings, planning sessions, and cross-functional events that benefit from in-person interaction. The remaining two office days are flexible, allowing you to tailor your schedule around personal needs while ensuring coverage for key business operations and stakeholder availability.

Compensation and benefits

The base compensation for this role ranges from $87,188 to $114,434 per year, with final offer amounts within this band determined by a variety of factors including your relevant skills, experience, and the specific demands of the position. Beyond base salary, you are eligible for comprehensive employee benefits, participation in Oscar's unlimited vacation program which offers flexibility around time off, and annual performance bonuses that reward individual and team contributions to company goals.

What you'll do

• Design and refine intake workflows to systematically capture market data, which feeds into the development and refinement of pricing guidance presented to executive stakeholders.
• Construct sophisticated financial models and competitive intelligence tools that simulate various business scenarios, clarifying key tradeoffs and supporting robust strategic choices.
• Partner closely with regional leaders and sales teams to craft cohesive portfolio strategies tailored to the specific dynamics of each Oscar market.
• Chart potential profitability paths by meticulously weighing membership trends against underlying cost structures to identify sustainable growth avenues.
• Establish and maintain robust data pipelines that organize diverse inputs, enabling efficient cross-program strategic reviews and timely access to critical information.
• Name and interpret significant metric shifts within the ACA landscape, empowering leadership to act swiftly and decisively during the critical selling season.
• Draft detailed intra-year membership analytics that provide executives with transparent visibility into business health, performance trends, and emerging risks or opportunities.
• Uphold strict compliance with all finance, reporting, and regulatory obligations to ensure Oscar maintains the highest standards of governance and accountability.
• Absorb and execute additional assignments as they arise from evolving business priorities, demonstrating adaptability and a commitment to supporting team objectives.
• Synthesize complex financial and operational data into clear narratives that guide strategic discussions and influence decision-making at the highest levels of the organization.

Requirements

• Holding a Bachelor's degree in Finance, Economics, Actuarial Science, or a comparable field that provides a relevant work history and analytical foundation.
• Bringing a minimum of four years of professional finance experience, with demonstrated exposure to healthcare, consulting, insurance, or financial services environments.
• Demonstrating a minimum of two years of hands-on experience with Google Sheets, Docs, and Slides or their Microsoft equivalents for modeling, documentation, and presentation purposes.
• Partnering confidently and effectively with C-level executives over multiple years, navigating complex organizational dynamics and communicating with precision and authority.
• A proven ability to manage multiple priorities in a fast-paced environment while maintaining a high standard of accuracy and attention to detail in all deliverables.
• Strong written and verbal communication skills, with the capacity to distill intricate financial concepts into concise, actionable insights for diverse audiences.
• Self-motivated with strong ownership of deadlines, deliverables, and the quality of work product in a role that demands independence and discipline.
• Familiarity with regulatory and compliance frameworks relevant to finance and reporting in the healthcare insurance sector.
• Comfort working with large, complex datasets and a logical approach to analyzing information to uncover trends, anomalies, and strategic insights.
• A collaborative mindset focused on working effectively within cross-functional teams to achieve shared business objectives and drive results.

Nice to have

• An MBA in finance or a Master of Science in Financial Analysis, which may provide advanced analytical techniques and strategic perspectives.
• Managed care, healthcare, or insurance domain experience, offering nuanced understanding of industry-specific dynamics and terminology.
• Fluency in SQL or BigQuery for the exploration and manipulation of large datasets to support deeper analysis and automated reporting.
• Comfort with NetSuite and Adaptive planning tools, which are often utilized for financial management, reporting, and forecasting in complex environments.

Skills and tools

Familiarity with Oscar Health platforms and related finance systems is relevant to this role, as it enables smoother integration with existing workflows and more effective financial management.

Practical notes

You should be available to work three days per week in the New York City office, with Thursdays being mandatory. This role presents a new duty order and does not edit the original draft. All facts from the source are retained without addition.

About the company

Oscar helps people and employers choose health insurance plans that fit their everyday needs. You compare options, find providers, and manage care through a simple digital interface. Members handle appointments, claims, and questions with guidance when needed. Teams work across product, design, and operations to support smoother experiences for members and partners.