Director, Paid Media

About the role

We are looking for a Director of Paid Media to lead a complex and evolving media ecosystem. This is not a traditional performance marketing role. You will sit at the Oscar Health corporate level and oversee paid media across products including Oscar Health insurance and our new Lucie marketplace. You'll navigate overlapping audiences, different distribution models (consumer vs. broker), and a highly regulated category where precision matters.

Responsibilities

• Establish the Foundation & the Innovation Lab
• Codify a "Gold Standard" operating model for media that stabilizes current performance and provides a clear baseline.
• Design a structured test-and-learn roadmap to explore new channels, creative formats, and beta opportunities, ensuring we aren't just maintaining, but evolving.
• Incorporate AI-driven tools and workflows to accelerate media planning, creative iteration, and predictive modeling, keeping Oscar at the forefront of marketing technology
• Bring Order to a Fragmented Media Ecosystem
• Establish a single, cohesive media strategy across Oscar and Lucie, unifying efforts split across teams and agencies.
• Define clear audience segmentation and channel roles to avoid duplication and internal competition.
• Create a framework for when and how we show up differently for brokers, members, and prospective customers.
• Own Performance in a Regulated, High-Stakes Category
• Drive efficient acquisition while protecting brand trust, balancing short-term performance with long-term credibility.
• Implement measurement approaches that account for longer conversion windows, offline influence, and broker-led decisions.
• Lead Agencies and Elevate Internal Capability
• Direct and unify external agencies supporting different parts of the business.
• Improve on media planning, rigor, and accountability across partners.
• Modernize our approach by identifying where AI and automation can replace manual tasks to free up the team for higher-level strategy.

Requirements

• Experience: 10+ years leading and building paid media in a complex, multi-stakeholder environment (healthcare, financial services, or similarly regulated categories).
• Strategic Balance: Experience managing both brand and performance investments, and knowing exactly when to lean into each.
• Tech-Forward Mindset: Familiarity with (and curiosity for) AI tools that drive efficiency in media buying, creative production, and data analysis to quickly advance our mission.
• Structural Thinking: Comfort navigating ambiguity and building structure where it doesn't yet exist.
• Analytical Rigor: A strong perspective on attribution, incrementality, and media effectiveness beyond platform reporting.
• Vendor Management: Experience managing multiple agencies and aligning them to a single, unified strategy.
• Leadership: A style that is hands-on & pragmatic