Engineering Leader

Hi, we're Oscar. We're hiring an Engineering Manager to join our Engineering team.

Oscar is the first health insurance company built around a full stack technology platform and a 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.

As an Engineering Manager, you will oversee every stage of engineering development, from conceptualization and design to rigorous testing and successful deployment, ensuring our engineering projects drive innovation and provide value. You'll lead engineers to help them design for stability, performance, and scalability across services or clients.

In this role, you will identify and solve the most valuable business problems by blending deep user empathy and sharp product intuition with a thorough understanding of Oscar’s operating model and business levers. You will serve as a strategic partner to engineering, data, and design to lead complex, cross-domain initiatives, ensuring direct alignment with senior leadership on priorities and outcomes. You will act as force multiplier—mentoring engineers, influencing product practices, and consistently raising the bar on technical quality, organizational clarity, and business impact.

Work Location: 

Oscar is a blended work culture where everyone, regardless of work type or location, feels connected to their teammates, our culture and our mission. 

If you live within commutable distance to our New York City office (in Hudson Square), our Tempe office (off the 101 at University Dr), or our Los Angeles office (in Marina Del Rey), you will be expected to come into the office at least three days each week. 

• Manage a team of engineers, focusing on professional development, performance management, and technical mentorship.
• Oversee the planning, execution, and delivery of complex technical projects, ensuring they meet deadlines and quality standards.
• Lead architectural decisions and technical design for full-stack applications.
• Partner with Product, Design, and other engineering leads to define roadmaps and solve business challenges.
• Promote best practices in software development, including code reviews, testing, and documentation.
• Identify and resolve bottlenecks in the development process to improve team velocity and system reliability.

• 6+ years of professional software engineering experience, working with a variety of technologies, and have increasingly impactful accomplishments.
• 2+ years of experience in engineering management or a technical lead role.
• Experience proposing, experimenting, and iterating, whether it be a new shiny technology or an arcane, ill-conceived data structure.
• Experience with technical contributions, improving the quality of what you create, and are excited to build fault-tolerant, and scalable software systems.
• Demonstrates solid understanding of the practical application of CS concepts within their team.
• Consistently writes stable, correct, and maintainable code with little oversight; writes modular, adaptable code with guidance.

• Advanced experience with frontend architecture and building end-to-end web applications.
• Proficiency in designing micro services, optimizing database performance, or working with distributed systems.
• Familiarity with integrating Machine Learning models, working with Large Language Models (LLMs), or building data-driven features.
• Background in healthcare or other highly regulated industries.

Pay Transparency:

The base pay for this role is: $163,944 - $215,176 per year. You are also eligible for employee benefits, participation in Oscar’s unlimited vacation program, company equity grants, and annual performance bonuses.