DevOps Engineer

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

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 Specialty Program Group:

Our goal is to partner with industry-leading specialty businesses to provide them with the ability to achieve their goals and optimize their businesses. Specialty Program Group offers access to capital and investment, deep carrier relationships, creative thinking, product development and broad distribution, while allowing our businesses to maintain the essence of what makes them successful. Specialty Program Group delivers leading-edge specialty expertise backed by transformative digital capabilities and sophisticated data and analytics.

About SquareMouth:

SquareMouth was launched in 2003 with the core goals of becoming the best workplace for its employees and the best place for customers to buy travel insurance. In 2014, we utilized our travel insurance expertise to develop and launch Tin Leg, a travel insurance brand with policies designed to address our customer’s most common and pressing travel concerns. Tin Leg quickly became one of the most popular travel insurance providers on squaremouth.com and continues to offer some of the most comprehensive products in the travel insurance market.

We’ve grown from a small team to a company of over 50 employees, gaining national and international recognition along the way as one of the best customer service teams and best places to work.  Widely recognized for our company culture, we are proud of most recently being named one of the Best Workplaces in America in 2023 by Inc. Magazine!

Continuing to strive toward our goal of being one of the most innovative companies in the field, SquareMouth was acquired in April 2023 by Specialty Program Group (SPG), a leading operator of specialty insurance brokerages and underwriting facilities. Today, Squaremouth.com, and its multi-award winning customer service team, has helped over 3 million travelers save time and money to find the best travel insurance policy for their trip.

Benefits:

• Salary range for this position is $90k-$120k, commensurate with experience

• 401(k) match

• Involvement in major Squaremouth decisions

• We are currently full time remote with optional office space in the Fort Wayne area

Disclosure required under applicable state or municipality regulations: The expected salary range for this position is $90,000-$125,000 and will be impacted by factors such as the successful candidate’s skills, experience and working location, as well as the specific position’s business line, scope and level. HUB International is proud to offer comprehensive benefit and total compensation packages which could include health/dental/vision/life/disability insurance, FSA, HSA and 401(k) accounts, paid-time-off benefits, and eligible bonuses, equity and commissions for some positions.

#SPG

HUB International Limited is an equal opportunity employer that does not discriminate on the basis of race/ethnicity, national origin, religion, age, color, sex, sexual orientation, gender identity, disability or veteran's status, or any other characteristic protected by local, state or federal laws, rules or regulations.

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