Lead Cloud & DevOps Engineer

Who is Cover Whale?

Cover Whale improves road safety by combining the insurance products we sell with our data-driven driver coaching and safety program. Our safety program is proven to save lives while delivering better insurance for our drivers.

Founded in 2019, Cover Whale recently closed a $27.5M Series A funding round with Morgan Stanley Expansion Capital and is continuing to scale and expand its business.  We were also acknowledged in Forbes as one of America's Best Startup Employers 2023 (forbes.com). For more information, please visit www.coverwhale.com. 

Join us in the mission!

The Role:

The Lead Cloud & DevOps Engineer will be a key technical leader responsible for architecting, building, and maintaining our cloud infrastructure while driving automation and operational excellence. In this role, you will lead the development of scalable cloud solutions and the continuous improvement of infrastructure and deployment processes.

You will collaborate closely with cross-functional teams to ensure our systems are secure, highly available, and optimized for performance. This position requires a strong strategic mindset, technical depth, and the ability to manage complex cloud environments and DevOps practices. As a senior member of the Engineering team, you will set the technical direction for cloud operations and DevOps, mentor Engineers, and ensure that our infrastructure scales efficiently with the company's growth.

Responsibilities:

• Architect and manage cloud infrastructure by designing, implementing, and maintaining scalable, secure, and cost-efficient environments in AWS, with a view toward potential multi-cloud strategies.
• Develop and lead the DevOps strategy, driving practices that optimize development velocity and operational efficiency through CI/CD automation, infrastructure as code (IaC), and effective release management.
• Build and maintain automated workflows for infrastructure provisioning, configuration management, and deployment pipelines to ensure operational efficiency.
• Implement monitoring, logging, and alerting systems that provide real-time visibility into system performance, ensuring high availability and uptime for production environments.
• Lead incident response and disaster recovery by proactively identifying potential vulnerabilities and developing automated backup, failover, and business continuity strategies.
• Embed security and compliance into infrastructure, partnering with security teams to integrate DevSecOps practices and ensure adherence to SOC 2, NYCRR Part 500, and other regulatory standards.
• Manage and optimize cloud costs by continuously evaluating resource usage, implementing cost-saving measures, and automating efficient scaling practices, with a focus on ongoing cloud resource forecasting.
• Collaborate closely with development, security, and product teams to align cloud architecture and DevOps practices with immediate and long-term business objectives.
• Provide leadership and mentorship to Engineers, fostering a culture of continuous improvement, innovation, and technical excellence.
• Evaluate and adopt emerging cloud and DevOps technologies, driving the adoption of innovative tools and best practices to enhance efficiency, scalability, and security.
• Lead and execute cloud migration efforts, ensuring the seamless transition of legacy systems while minimizing downtime and optimizing performance.

Compensation:

The Expected base pay for the role will be $150,000 to $200,000K per year at the commencement of employment. However, base pay if hired will be determined on an individualized basis and is only part of the total compensation package, which, depending on the position, may also include discretionary bonus and other Cover Whale-sponsored total rewards/benefits.

Requirements

Please Note: At this time, Cover Whale is unable to provide immigration visa support for this position. Candidates must be authorized to work in the United States on a full-time basis without the need for sponsorship.

Education and Experience:

• Bachelor’s degree in Computer Science, Information Technology, Engineering, or a related field or equivalent industry experience in cloud infrastructure and DevOps roles.
• 7+ years of experience in cloud architecture, DevOps, or a similar technical field, focusing on designing, implementing, and managing scalable cloud environments.
• 5+ years of hands-on experience with Amazon Web Services (AWS), including deep expertise in AWS EKS (Elastic Kubernetes Service), RDS (Relational Database Service), and other AWS cloud services.

Must-Have Skills/Abilities:

• Proven experience with Pulumi or other Infrastructure-as-Code (IaC) tools to automate and manage cloud infrastructure.
• Extensive experience with Kubernetes for container orchestration, including deploying, managing, and scaling workloads in AWS EKS.
• Experience in Grafana Cloud for incident response management, alerting, logging, and observability, with the ability to implement and manage real-time monitoring and alerting solutions.
• Extensive experience in designing and managing CI/CD pipelines using modern DevOps tools such as GitHub Actions integrated with Kubernetes and AWS environments.
• Strong scripting skills in Go, Python, Bash, or similar languages.
• In-depth knowledge of disaster recovery and business continuity practices, including backup strategies, failover processes, and system restoration in cloud environments.
• Solid understanding of security best practices and experience with DevSecOps processes, with working knowledge of compliance requirements such as SOC 2, NYCRR Part 500, or similar regulatory frameworks.
• In-depth knowledge of disaster recovery and business continuity practices, including backup strategies, failover processes, and system restoration in cloud environments.
• Demonstrated leadership experience, including mentoring and guiding Engineering teams, driving best practices, and fostering a culture of collaboration and innovation.
• Excellent communication skills with the ability to work cross-functionally with teams such as product, security, and development to align technical strategies with business goals.

Preferred but not required:

• Certifications in cloud platforms, such as AWS Certified Solutions Architect, AWS Certified DevOps Engineer, or equivalent in GCP or Azure.
• Experience in multi-cloud or hybrid-cloud environments and understanding of cloud vendor trade-offs and benefits.
• Knowledge of cost management tools and strategies for optimizing cloud spend (e.g., AWS Cost Explorer, Spot Instances, etc.).

Benefits

• Health Care Plan (Medical, Dental & Vision)
• Retirement Plan (401k, IRA)-match
• Life Insurance (Basic, Voluntary & AD&D)
• Paid Time Off (Vacation, Sick & Public Holidays)
• Paid Family Leave (Maternity, Paternity)
• Tuition Assistance
• Professional Training & Development