DevOps 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.

As a DevOps Engineer, you will play a key role in supporting the development, deployment, and maintenance of our software and infrastructure. Working closely with software engineers, system administrators, and IT teams, you'll help automate processes, improve deployment pipelines, and ensure the reliability and performance of production environments. This role is ideal for someone who enjoys solving technical challenges, streamlining operations, and contributing to modern DevSecOps practices. You'll have the opportunity to support cloud and infrastructure initiatives while helping drive continuous improvement across our engineering environment.

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

Key Responsibilities

Cloud Infrastructure (AWS)

• Design, implement, and manage scalable, secure AWS infrastructure.
• Maintain infrastructure as code (IaC) using tools such as Terraform or CloudFormation.
• Optimize infrastructure for performance, reliability, and cost efficiency.
• Manage networking, access controls, and environment configurations across dev, staging, and production.

CI/CD & Automation

• Build and maintain automated CI/CD pipelines to support reliable and repeatable deployments.
• Improve deployment speed, quality, and rollback capabilities.
• Implement automation to reduce manual processes across infrastructure and operations.
• Partner with engineering teams to ensure smooth release processes and environment consistency.

Site Reliability Engineering (SRE) & System Health

• Own system reliability, uptime, and performance across all environments.
• Define and monitor SLIs/SLOs and key system health metrics.
• Implement observability practices including logging, monitoring, and alerting.
• Lead incident response, root cause analysis (RCA), and continuous improvement of system stability

Security & Compliance

• Implement and maintain security best practices across infrastructure and pipelines.
• Manage identity and access controls (IAM), secrets, and data protection.
• Ensure systems meet relevant compliance requirements (e.g., SOC 2, PCI as applicable).
• Partner with engineering to embed security into the development lifecycle.

Cost Management & Optimization

• Monitor and manage AWS spend, ensuring cost visibility and accountability.
• Identify and implement cost optimization opportunities without compromising performance.
• Establish cost controls, budgets, and alerts.

Collaboration & Enablement

• Work closely with Engineering, QA, and Product teams to support delivery and operational needs.
• Provide guidance on infrastructure, deployment, and reliability best practices.
• Enable teams with self-service tools and clear documentation.

Documentation & Standards

• Maintain documentation for infrastructure, pipelines, and operational procedures.
• Establish and enforce standards for deployment, monitoring, and incident management.

Skills and Experience Needed:

• Education: Bachelor's degree in computer science or related field, or equivalent combination of education and experience.
• 2+ years of experience in DevOps, Site Reliability Engineering, or cloud infrastructure roles.
• Strong hands-on experience with AWS services (EC2, ECS/EKS, RDS, S3, VPC, IAM, CloudWatch, etc.).
• Experience with infrastructure as code (Terraform, CloudFormation, or similar).
• Experience building and maintaining CI/CD pipelines (e.g., GitHub Actions, GitLab CI, Jenkins).
• Experience with monitoring and observability tools (e.g., Datadog, CloudWatch, Prometheus/Grafana).
• Solid understanding of system reliability, incident management, and root cause analysis.
• Experience implementing security best practices in cloud environments.

Preferred

• Experience in ecommerce or high-traffic digital platforms.
• Familiarity with containerization and orchestration (Docker, Kubernetes).
• Experience with compliance frameworks (SOC 2, PCI DSS).
• Knowledge of cost management tools and practices in AWS.
• Scripting or programming experience (Python, Bash, etc.).

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 $93,400 - $140,200 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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