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!

InsureMyTrip is looking for a Principal Software Engineer to drive architectural execution and lead a high-performing engineering team. This person will design, modernize, and scale complex ecommerce systems; while ensuring reliable delivery, strong engineering standards, and long-term platform health aligned with company growth.

1. Hybrid
2. Eleven company-paid holidays plus 20 PTO days
3. 401(k) Retirement Plan with 6% company match
4. Available health, dental, and vision insurance plans

The Adventure Ahead:

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

Skills and Experience Needed:

1. 4 year / Bachelors Degree in Computer Science or similar field
2. 6 years of professional software engineering experience, including architectural leadership and team development
3. Proven experience designing and scaling distributed systems and high-traffic ecommerce applications.
4. Strong proficiency in PHP and Python, with experience building microservices and integrating with WordPress-based platforms
5. Strong database expertise (MySQL, PostgreSQL), including schema design, indexing, query optimization, and performance tuning.
6. Experience with caching, search, and event-driven data stores (e.g., Redis, Elasticsearch).
7. Hands-on experience with AWS and infrastructure-as-code practices.
8. Strong DevOps knowledge, including CI/CD, automated testing, and safe deployment practices.
9. Experience optimizing ecommerce performance (caching, async processing, background jobs, API efficiency).

If your experience aligns with this position, please apply!

InsureMyTrip is an equal-opportunity employer. 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.

The pay range for this position is $131,100 - $196,700 which includes geographic adjustments, where applicable. The pay range is the range THMCC, in good faith, believes is the range of compensation for this role at the time of this posting. The hired applicant will be offered pay within the entire range based on the candidate’s geographic location, qualifications, work experience, education, and/or skill level. The Company is fully committed to ensuring equal pay opportunities for equal work regardless of color, race, sex, national origin, sexual orientation, religion, age, veteran status, disability, pregnancy, citizenship status, genetic information, or any other basis protected by federal, state, or local pay equity laws.

You do not need to disclose your criminal history or participate in a background check until a conditional job offer is made to you. After making a conditional offer and running a background check, if the Company is concerned about a conviction that is directly related to the job, you will be given the chance to explain the circumstances surrounding the conviction or challenge the accuracy of the background report.

As an insurance company, we comply with certain federal, state and local laws such as the Violent Crime Control and Law Enforcement Act of 1994 (18 USC § 1033(e)), which restricts our ability to employ individuals with certain types of criminal convictions. Where not restricted by law and for criminal history not covered by this law, the Company will consider qualified applicants with arrest or conviction history in compliance with applicable law.

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