Staff Product Manager, AI

Hi, we're Oscar. We're hiring a Staff Product Manager to join our AI 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 Staff Product Manager is a senior individual contributor role responsible for defining and driving complex, technical product initiatives with strategic impact across the organization. In this role, you will identify and solve the most valuable business problems through deep user empathy, sharp product intuition, and a strong understanding of Oscar’s operating model and business levers. You will partner closely with engineering, data, and design to lead complex initiatives across domains, aligning directly with senior business leaders on priorities and outcomes. You will act as a force multiplier within the organization—mentoring peers, influencing product practices, and consistently raising the bar on quality, clarity, and impact.

In this Staff Product Manager role, you will focus on AI research and development. You’ll work closely with a small team of engineers and data scientists to explore and prototype new concepts and workflows across Oscar.

You will report into the Senior Director, AI.

Work Location:

This is a remote position, open to candidates who reside in: Boston, MA. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area.

Pay Transparency:

The base pay for this role is: $180,504.00 - $236,911.50 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

• Helping to define the vision, strategy and roadmap for tech components, workflows, and insights that make it easy for teams across Oscar to leverage AI.


• Partnering closely with stakeholders including cross functional department leaders across the business to define strategy and roadmap.


• Collaborating with Engineering and Product leadership to make resource trade-off decisions and to ensure teams are working together effectively.


• Provide recommendations to leadership for product enhancements to improve existing products and development of new ones.


• Develop operating models for new products in partnership with leadership.


• Compliance with all applicable laws and regulations.


• Other duties as assigned.

Requirements:

• 7+ years of Product Management experience.


• 1+ years of Product Management experience in an AI or healthcare setting.


• Experience building a net new product 0-1.

Bonus points

• Experience developing AI or ML-related features strongly preferred.


• Experience building AI infrastructure.


• SQL skills strongly preferred.


• Comfort in working in highly collaborative environments while ensuring the team is always driving towards a decision.


• Excellent analytical and quantitative skills; proved experience using data to identify opportunities, test theories and evaluate success.


• Experience as an end-to-end thinker; the ability to look at a problem and create a solution all the way from top-level goals to smaller details.


• Ability to influence and manage stakeholders at all levels and experience working across all levels of leadership using strong communication and structured thinking.