Senior Software Engineer

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. Joining the InsureMyTrip Team means having the advantages of being part of a leading company while enjoying many of the benefits more typical of a startup culture. You’ll have the ability to make an impact, influence key strategic decisions and create or change processes.

The Senior Software Engineer is responsible for leading the design, development, modernization, and operational excellence of scalable digital commerce solutions that power our customer experience. This role serves as a senior technical contributor who drives complex initiatives end-to-end, ensures high-quality execution, and elevates engineering standards across the team. The Senior Software Engineer partners closely with Product, UX, QA, DevOps, and Site Reliability Engineering teams to deliver secure, reliable, and high-performing ecommerce capabilities for our Digital Commerce Platform.

This position plays a key role in architectural decisions, technical design documentation, production stability, performance optimization, and mentoring engineers while ensuring consistent, high-quality delivery aligned with business priorities.

This role is Hybrid, you must be able to come into Warwick, RI office.

Key Responsibilities

Technical Leadership & Delivery

• Lead the design and implementation of complex ecommerce features and platform enhancements.
• Break down large, ambiguous initiatives into clear, actionable technical tasks and drive execution across contributors.
• Own delivery of projects from technical design through production release and post-launch support.
• Identify risks, dependencies, and trade-offs early; propose pragmatic solutions to ensure timely delivery.
• Provide technical guidance and mentorship to engineers, promoting engineering excellence and best practices.

Software Development

• Design, develop, test, and maintain high-availability ecommerce applications and services.
• Contribute across backend and frontend systems, supporting both legacy stabilization and modern architecture initiatives.
• Write clean, maintainable, scalable, and well-tested code following established engineering standards.
• Lead and participate in code reviews, raising overall code quality and maintainability.
• Drive continuous improvement in development practices, tooling, and standards.

Architecture & System Design

• Design scalable, secure, and resilient systems that support high-transaction digital commerce environments.
• Lead architectural discussions and contribute to API-first, event-driven, and cloud-native modernization efforts.
• Evaluate new technologies and make recommendations aligned with long-term platform strategy.
• Identify and resolve performance bottlenecks, scalability constraints, and reliability gaps.
• Design and oversee integrations with third-party systems (payments, pricing, CRM, fulfillment, etc.).

Software Design & Documentation

• Develop and maintain comprehensive software design documentation, including technical specifications, architecture diagrams, API contracts, and integration of flows.
• Ensure documentation enables knowledge sharing, onboarding, and long-term maintainability.
• Lead design reviews and ensure alignment with established architectural standards.
• Document system changes and ensures traceability from requirements through implementation.

Site Reliability & Operational Excellence

• Apply Site Reliability Engineering (SRE) principles to improve reliability, scalability, and operational maturity.
• Define and support service level objectives (SLOs), service level indicators (SLIs), and reliability targets.
• Drive improvements in monitoring, logging, alerting, and observability.
• Lead troubleshooting of complex production incidents and conduct root cause analysis with clear corrective actions.
• Participate in and help mature on-call practices.
• Improve system resilience through automation, performance optimization, and proactive reliability engineering.

Performance & Optimization

• Monitor and optimize site performance using modern web performance metrics, including Core Web Vitals (LCP, FCP, INP) and percentile-based thresholds (e.g., p75).
• Drive measurable improvements in page performance, API latency, and system throughput.
• Use data-driven insights to recommend and implement performance enhancements.

Collaboration & Cross-Functional Partnership

• Partner with Product Management to shape technical solutions that align with business outcomes.
• Work closely with QA to ensure strong automated test coverage and release quality.
• Collaborate with DevOps to enhance CI/CD pipelines, deployment reliability, and cloud infrastructure.
• Actively contribute to sprint planning, retrospectives, and technical roadmap discussions.
• Provide clear, professional communication across engineering and business stakeholders.

Skills and Experience Needed:

• Education: Bachelor's degree in computer science or related field, or equivalent combination of education and experience.
• 5+ years of software development experience.
• Proven experience delivering complex software projects in production environments.
• Strong proficiency in at least one backend language (e.g., Java, .NET, Node.js, Python) and/or modern frontend framework (e.g., React, Angular, Vue), as well as experience with PHP and JavaScript.
• Experience designing and building web applications and APIs in distributed systems environments.
• Strong understanding of system design, RESTful services, and integration patterns.
• Experience with relational and NoSQL databases.
• Demonstrated ability to break down complex initiatives into clear technical plans and executable tasks.
• Experience contributing to or leading technical design documentation.
• Experience supporting production systems, troubleshooting incidents, and improving operational reliability.

Preferred

• Experience working in ecommerce or other high-transaction digital platforms.
• Experience with cloud platforms (AWS, Azure, or GCP).
• Familiarity with CI/CD pipelines and DevOps practices.
• Experience with containerization (Docker, Kubernetes).
• Experience monitoring and optimizing site performance using Core Web Vitals (LCP, FCP, INP) and percentile-based performance metrics (e.g., p75 thresholds).
• Familiarity with observability tools (Datadog, New Relic, Grafana, Prometheus, Google Lighthouse, or similar).
• Experience with SRE concepts such as SLOs, SLIs, error budgets, and incident management.
• Understanding of web application security best practices and secure coding standards.

What We Offer

• Hybrid Schedule, 2 days work from home and 3 days in office (fully remote work not available)
• Strong learning culture with ongoing development opportunities
• Comprehensive medical, vision, and dental coverage, with eligibility beginning on your first day of employment
• Basic life and disability insurance
• 401(k) plan with 6% company match
• 20 days of PTO, two floating holidays, approximately 11 paid holidays, and volunteer time off
• Paid parental leave
• Access to our award-winning wellness program, including mental health services, fitness network membership, and a complimentary Headspace subscription
• Student loan matching program

If you are a motivated professional with the skills and experience to succeed in this role, we encourage you to apply and join our team. Join a team where your success is our priority and you can make a real impact!

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 $104,600 - $157,000 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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