Principal Software Engineer

Job Summary

As the nation’s original travel insurance comparison site, InsureMyTrip, a member of the Tokio Marine HCC group of companies, has over 20 years of experience connecting travelers with the best trip policy. Additionally, Providence Business News named InsureMyTrip a 2023 Top Workplace Winner!

About the Role

Lead the design and delivery of scalable, resilient ecommerce systems, modernizing legacy components into clean, modular architectures.

Responsibilities

• Own end-to-end execution of complex technical initiatives with a focus on quality, predictability, and operational excellence.
• Manage and develop a small team of engineers, driving accountability, ownership, and consistent delivery standards.
• Contribute directly to architecture and production code, setting a high technical bar through design reviews and hands-on guidance.
• Establish and reinforce strong engineering practices, including API-first design, automated testing, CI/CD rigor, and infrastructure as code.
• Embed reliability and SRE principles into workflows, including observability, SLIs/SLOs, incident management, and continuous improvement.
• Reduce technical debt through pragmatic modernization that improves long-term platform health without slowing delivery.
• Partner with Product and company leadership to align technical decisions with business priorities and growth objectives.
• Support hiring, mentoring, and performance development to build a strong, delivery-focused engineering culture.

Requirements

• 4 year / Bachelors Degree in Computer Science or similar field
• 6 years of professional software engineering experience, including architectural leadership and team development
• Proven experience designing and scaling distributed systems and high-traffic ecommerce applications
• Strong proficiency in PHP and Python, with experience building microservices and integrating with WordPress-based platforms
• Strong database expertise (MySQL, PostgreSQL), including schema design, indexing, query optimization, and performance tuning
• Experience with caching, search, and event-driven data stores (e.g., Redis, Elasticsearch)
• Hands-on experience with AWS and infrastructure-as-code practices
• Strong DevOps knowledge, including CI/CD, automated testing, and safe deployment practices
• Experience optimizing ecommerce performance (caching, async processing, background jobs, API efficiency)

Qualifications

InsureMyTrip is an equal-opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry, citizenship, color, family or medical care leave, gender identity, genetic information, marital status, medical condition, national origin, physical or mental disability, protected veteran or military status, race, ethnicity, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable local laws, regulations and ordinances.

Benefits

Eleven company-paid holidays plus 20 PTO days
401(k) Retirement Plan with 6% company match
Available health, dental, and vision insurance plans

Pay

The pay range for this position is $131,100 - $196,700 which includes geographic adjustments, where applicable.

Schedule

Hybrid Only - Warwick, Rhode Island