Director, Paid Media

Hi, we're Oscar. We're hiring a Director, Paid Media to join our Corporate Marketing 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:

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.

Work Location: This position is based in our New York City 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: $180,504 - $236,911 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

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.
• Operate at the Intersection of Brand, Growth, and Distribution
  • 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.
• 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.
• Compliance with all applicable laws and regulations.
• Other duties as assigned.

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, incremen