Director of Paid Media

Responsibilities 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 The mission is to set a rock-solid foundation of "what works" today while carving out the space to innovate, test, and learn into the strategies of tomorrow You’ll be responsible for defining how media works end-to-end at Oscar - from national brand investment to targeted acquisition - ensuring our dollars work as hard as possible across the entire enterprise You will report into the Senior Director 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 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 Build media plans that reflect the realities of health insurance decision-making cycles (seasonality, OEP, broker influence, life events) Partner with growth, product, and sales to align media with how people actually choose coverage, not just how we market it Ensure Lucie and Oscar are positioned intentionally- never competing for the same attention with conflicting messages 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 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 Compliance with all applicable laws and regulations Other duties as assigned Qualifications & Experience 10+ years leading and building paid media in a complex, multi-stakeholder environment (healthcare, financial services, or similarly regulated categories) Experience managing multiple agencies and aligning them to a single, unified strategy Experience managing both brand and performance investments, and knowing exactly when to lean into each Comfort navigating ambiguity and building structure where it doesn’t yet exist Familiarity with (and curiosity for) AI tools that drive efficiency in media buying, creative production, and data analysis Hands‑on, pragmatic leadership style that balances strategic thinking with execution Strong perspective on attribution, incrementality, and media effectiveness beyond platform reporting Healthcare experience or familiarity with regulated categories such as health insurance #J-18808-Ljbffr Oscar Health