Job Description

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

• Monitor, maintain, and support production software systems and services.
• Develop and maintain local development, testing, and QA environments.
• Build and enhance automation tools and deployment pipelines to improve software delivery.
• Support infrastructure modernization initiatives, including Infrastructure as Code (IaC).
• Collaborate with software developers, system administrators, and cross-functional IT teams.
• Troubleshoot deployment and infrastructure issues while identifying opportunities for process improvements.
• Assist with the planning, deployment, and maintenance of enterprise IT infrastructure.
• Contribute to continuous improvement initiatives that enhance system reliability, efficiency, and scalability.

Skills and Experience Needed:

• Bachelor's degree in Computer Science, Information Technology, or a related field (or equivalent combination of education and experience).
• 2+ years of experience supporting software deployments in a DevOps or similar environment.
• Experience with Linux environments; 5+ years preferred.
• Proficiency with scripting and automation languages such as Bash, Python, or PHP.
• Experience with infrastructure and deployment automation tools such as Terraform, Ansible, Chef, or Puppet.
• Knowledge of database technologies including MySQL/MariaDB, MongoDB, or Redis.
• Strong analytical, problem-solving, and organizational skills.
• Excellent written and verbal communication skills with the ability to collaborate across technical teams.
• Ability to manage multiple priorities in a fast-paced environment while maintaining attention to detail.

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.