Remote Tooling Manager Jobs in California (NOW HIRING)

Hi, we're Oscar. We're hiring a Group Product Manager, Member Coverage & Support Platform to join our Product 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:

Getting health insurance right is one of the most important ways Oscar serves its members. Members need to enroll smoothly, understand and pay their bills, and get fast, effective support when something goes wrong. Behind those moments is a complex set of platforms, integrations, workflows, and tools that connect our members and internal teams.

We're hiring a Group Product Manager to lead the product team responsible for the platforms that help members get covered and get the support they need. This role will own a large and technically complex product area spanning coverage data integrations and APIs, billing and payment workflows, and the tools our support teams use to resolve member issues.

As Group Product Manager, you will set the vision and strategy for a critical part of Oscar's operating model. You will help modernize legacy tooling, improve the end-to-end member and agent experience, and ensure our platforms can scale through seasonal peaks and high-pressure moments in the healthcare calendar.

This is a deeply cross-functional role. You will partner with Engineering, Operations, Data, Design, and business leaders to connect strategy to execution across technical systems and human workflows. You will need to understand the whole machine, translate complex systems for non-technical audiences, and make thoughtful tradeoffs across member experience, operational performance, platform reliability, and business needs.

You will also lead and develop a team of product managers.

You will report into a Director of Product Management.

Work Location:

This is a remote position, open to candidates who reside in: San Francisco, CA. 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. #LI-Remote

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:

• Define the vision, strategy, and roadmap for Oscar's Member Coverage & Support platforms.
• Lead product strategy across technical systems that support member coverage, billing, payments, service workflows, integrations, and APIs.
• Manage, mentor, and develop a team of product managers
• Partner with Engineering, Operations, Data, Design, and business leadership to modernize legacy tools and improve platform scalability, usability, and reliability.
• Improve the tools and workflows that help support teams resolve complex member issues quickly and accurately.
• Drive measurable improvements in operational and member experience outcomes, including first call resolution, call duration, escalation rates, and issue resolution quality.
• Develop product strategies for an evolving support model, including increased use of AI for simpler inquiries and a growing need for human agents to handle more complex cases.
• Translate complex technical and operational concepts into clear priorities, recommendations, and narratives for non-technical stakeholders.
• Make thoughtful roadmap and resource tradeoff decisions across a broad, seasonal, and business-critical product surface.
• Identify opportunities to reduce operational friction, improve agent effectiveness, and create a more seamless end-to-end member journey.
• Compliance with all applicable laws and regulations.
• Other duties as assigned.

Requirements:

• 7+ years of product management experience.
• 2+ years of people management experience.
• Experience leading technical platform products, internal tools, workflow systems, APIs, or integrations.
• Experience managing complex product areas with multiple stakeholders, systems, and operational dependencies.
• Strong communication skills, including the ability to translate technical complexity into clear business and product strategy.
• Strong analytical skills and experience using data to identify opportunities, prioritize work, and measure success.

Bonus points:

• Experience in healthcare, insurance, fintech, or another regulated and operationally complex industry.
• Experience improving support operations through tooling, automation, AI, workflow redesign, or agent-facing products.