Senior Principal Engineer

As a Senior Principal Engineer at Oscar, your primary responsibilities include collaborating with leadership to tackle complex business challenges with effective technical solutions, providing guidance to the Tech Leadership team, and ensuring alignment of Oscar's technology vision with business objectives. You'll also mentor other engineers, define coding standards, and oversee system integrations, making sure everything runs smoothly across our engineering efforts.

To be considered for the Senior Principal Engineer role at Oscar, candidates should have at least 15 years of experience in software engineering. A strong background in leading engineering teams, knowledge of emerging technologies, and a deep understanding of software architecture principles are also essential to ensure you can handle the role's responsibilities effectively.

At Oscar, we are committed to fostering the professional growth of our Senior Principal Engineers. This includes opportunities to mentor junior engineers, participate in ongoing training, and stay informed about industry trends. We believe that continuous learning and collaboration are key to innovation, and we actively encourage our team members to pursue professional development.

Oscar promotes a blended work culture for the Senior Principal Engineer position where flexibility meets connection. If you’re within commuting distance of our NYC, Tempe, or LA offices, we encourage in-person interaction a couple of days a week. For remote workers, we ensure that everyone feels connected with regular communication and team-building activities, making it an inclusive and supportive work environment.

As a Senior Principal Engineer at Oscar, you can look forward to a comprehensive benefits package that includes medical, dental, and vision coverage, an unlimited vacation program, 401(k) participation, performance bonuses, and even paid wellness time. We strive to ensure that our employees feel valued and supported in all aspects of their work and life.

In responding to this question, it's important to highlight specific examples where you successfully led a team to complete significant projects. Discuss your leadership style, how you motivate your team, and how you handle conflicts or challenges that arise.

For this question, share your understanding of Oscar’s business objectives. Discuss how you analyze goals, collaborate with stakeholders, and formulate a cohesive technology strategy that drives results, ensuring you provide examples of past successes.

Demonstrate your commitment to continuous learning by discussing the resources you use, such as industry journals, conferences, or online courses. Explain how you evaluate and integrate new technologies in past roles to benefit the organization.

Provide a specific example where you identified a complex challenge and the steps you took to resolve it. Discuss your analytical process and the technical solutions you implemented, along with the outcome and lessons learned from the experience.

Discuss the coding standards, methodologies (like Agile or Scrum), and development processes you believe are effective in producing high-quality software. Provide insights into how you ensure team adherence to these practices and your experience in implementing them.

In your answer, showcase your mentoring philosophy, detailing specific examples of how you’ve guided junior engineers in the past. Highlight the importance of fostering an inclusive learning environment and offering constructive feedback.

Discuss your methods for assessing project urgency and importance, using tools or frameworks that help you prioritize effectively. Share instances where you balanced multiple tasks, and the strategies that led to successful project completions.

Emphasize the value of teamwork in your projects. Discuss examples of successful collaboration with other departments such as Product Management or Data, and how these partnerships improved product outcomes.

Talk about your approach to designing scalable software architectures, including your considerations for future needs. Share relevant experiences where you successfully implemented scalable solutions.

Use this question to highlight your experience with innovation. Share examples of new processes, tools, or technologies you introduced and the positive impacts they had on the organization.