IT WOULD BE GREAT IF YOU HAVE EXPERIENCE WITH:

• Infrastructure as Code tools (e.g., Terraform, CloudFormation)
• Configuration management tools like Chef, Puppet, or Ansible
• Managing containerized environments using Docker and Kubernetes
• Operating within AWS, including services such as EC2, EKS, RDS, S3, and IAM
• Running and scaling web applications built on LAMP or similar stacks in cloud environments
• Working with databases—both relational (MySQL, PostgreSQL) and NoSQL (Redis, DynamoDB)—including performance optimization and availability strategies
• Writing and maintaining automated regression, integration, and deployment tests
• Comfort using MacOS/Linux terminals and scripting for automation
• Experience with Ruby, Python, or other scripting languages for DevOps tooling and automation
• Familiarity with using JAMF to manage policies and deploy updates to macOS devices

ABOUT THE ROLE:

Squaremouth’s mission is to take complicated insurance products and make it easy for travelers to compare them and find exactly what they need for peace of mind away from home — and our engineers are an essential part of building that experience.
We are looking for a DevOps Engineer to help enhance our cloud infrastructure and in-house tools, focusing on increasing resiliency, scalability, and performance as our systems grow. This role also plays a key part in shaping the next generation of our infrastructure.
Our current stack is based in Amazon Web Services, with internal tooling primarily written in Ruby. We use containerized services orchestrated with Docker, and value infrastructure automation as much as we value clean, readable code.

WHAT YOU’LL DO:

• Design, build, and improve infrastructure automation scripts for service orchestration, deployment, and monitoring, ensuring compliance with cloud security and data protection best practices
• Deploy, scale, and maintain cloud-native systems in AWS, with a focus on high availability, fault tolerance, and performance
• Manage and support Kubernetes clusters and containerized application environments, including rollout strategies, monitoring, and incident response
• Collaborate with developers to refine CI/CD pipelines, streamline deployment workflows, and optimize developer experience
• Write clean, well-documented infrastructure code and implement Infrastructure as Code (IaC)
• Monitor application and system metrics using logging, tracing, and alerting tools, and assist teams with performance tuning and troubleshooting
• Present findings, infrastructure updates, or emerging technologies to the broader team to promote transparency and continuous learning
• Continuously improve internal tools used for managing infrastructure, provisioning environments, and supporting deployment automation

WHAT WILL HELP YOU SUCCEED IN THIS ROLE:

• 3-5 years of professional experience managing scalable and highly available infrastructure – virtualization, cloud, networking, or storage services
• Ability to work independently while collaborating effectively within a distributed team
• Experience managing Linux-based systems and supporting modern web applications in production environments
• A passion for solving interesting problems, learning new technologies, and improving engineering workflows
• Strong communication skills and a positive, team-oriented attitude