Lead DevOps Engineer (Remote Optional) at Cover
Toronto, Ontario, CA / Remote
Think insurance is boring? We did too. So we built a company that takes everything you think you know about buying insurance and turns it on its head. 
At Cover, we want to become the largest and most customer centric insurance company in the world. 
Founded in 2016, Cover is a mobile-first insurance platform licensed in all 50 states, working with over 35 carriers. We were part of Y Combinator’s W16 batch, and have gone on to raise $27 million across three funding rounds backed by world class investors. 
We’re growing fast. In the past year we’ve scaled the team across our San Francisco and Toronto offices. Across our diverse and multi-skilled team we’re working together to deliver a service that’s effortless to interact with, transparently priced, and built on a sustainable and long term footing.
We’re pushing hard to make our vision of insurance a reality and we want dedicated, inquisitive and collaborative people who are ready to play their part in achieving our goal.
Cover is looking for an DevOps leader to work alongside our developers and help make sure our infrastructure is available and ready to grow as our needs dictate. We believe DevOps is a culture of co-operation where the developers are able to handle the deployment of code as often as possible and work with Ops to make sure that the code is deployable. The ideal candidate will also always be looking ahead to what new technology we can leverage to improve our deployment process, and be open to mentoring our developers around best practices.


    • Lead and build the DevOps practice at Cover with a focus more on the Ops side
    • Build the development culture around DevOps
    • Mentor our development teams on how to get software out to our users with a focus on how to make software production ready
    • Assist with CI/CD practices, consulting with our teams on their approach
    • Assist with migrating older software to our new infrastructure
    • Manage and improve on our existing infrastructure to meet the needs of our products, users and engineers
    • Experience with configuring Kubernetes to deploy projectsExperience using Jenkins to configure and build CI/CD pipelines

What We Use

    • Stack: AWS/EKS, Kubernetes, Jenkins, Docker, Elasticsearch, Grafana, Prometheus, Kibana
    • Focus on Infrastructure as code and configuration as code

Skills & Qualifications

    • Previous experience with IT Operations (2+ years)
    • Experience leading a DevOps team
    • Experience with the tools we use in our stack
    • Drive to bring a DevOps culture to our development teams
    • Strong ability to research and apply information found online in relation to new tools from official docs, articles, forums, etc
    • Driven to build and present Proof-of-Concepts showing new features or tools that we can use
    • Development skills to build fixes and custom parts to suite the needs of the company
    • Experience with deploying and managing Go and Rails apps (bonus points!)
    • Built DevOps teams and practices at previous companies (bonus points!)
We Believe in Equal Opportunity
We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, colour, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.