Director, Cloud Migration

Plymouth Rock Assurance is seeking an experienced and visionary Director of Cloud Migration to lead our dynamic team in a major AWS migration initiative. The successful candidate will be instrumental in shaping and executing our cloud strategy, ensuring the seamless transition of our IT infrastructure to AWS. This role requires a proven track record in cloud engineering, strong leadership skills, and expertise in AWS services and best practices.

Essential Functions and Responsibilities:

• Drive the planning, design, and implementation of our AWS migration strategy, collaborating with stakeholders to align with business goals.
• Manage and lead a team of skilled cloud architects, cloud engineers and DevOps engineers, providing guidance, mentorship, and support to ensure the successful delivery of cloud solutions.
• Utilize best practices and methodologies to implement AWS foundation architecture including Control Tower and Landing Zones.
• Implement effective Infrastructure as Code (IaC) strategies and standards for provisioning and managing AWS resources.
• Lead and contribute to the design and implementation of DevOps practices.
• Oversee the development and implementation of automation scripts for deployment, configuration, and orchestration of AWS infrastructure.
• Lead implementation of CI/CD pipelines for automated software delivery.
• Establish and enforce security measures to ensure the integrity and confidentiality of data, and compliance with industry standards and regulations.
• Collaborate with cross-functional teams, including operations, development, and other stakeholders, to plan and implement migration of applications to AWS.
• Monitor and optimize AWS infrastructure for performance, scalability, and cost-effectiveness.
• Document migration processes, best practices, and configurations to ensure knowledge transfer and continuity.
• Conduct training sessions and foster continuous improvement within the cloud engineering team.
• Provide detailed and transparent reports on the progress of the AWS migration initiative, communicating key metrics, challenges, and risks to stakeholders.

Qualifications and Education:

• Bachelor's or Master's degree in Computer Science or a related field.
• 8+ years of professional experience in cloud engineering, with a focus on AWS.
• Proven experience leading cloud engineering and DevOps teams, with a minimum of 5 years in a leadership role.
• Expertise in AWS services, particularly in migration projects.
• Expertise in implementing AWS foundation architecture.
• Strong understanding of IaC, automation, and scripting tools for AWS (e.g., Terraform, AWS CloudFormation).
• Experience with security best practices and compliance in AWS environments.
• Excellent problem-solving and troubleshooting skills.
• Effective leadership and communication skills to collaborate with cross-functional teams.

About the Company:

The Plymouth Rock Company and its affiliated group of companies write and manage over $2 billion in personal and commercial auto and homeowner’s insurance throughout the Northeast and mid-Atlantic, where we have built an unparalleled reputation for service. We continuously invest in technology, our employees thrive in our empowering environment, and our customers are among the most loyal in the industry. The Plymouth Rock group of companies employs more than 1,900 people and is headquartered in Boston, Massachusetts. Plymouth Rock Assurance Corporation holds an A.M. Best rating of “A-/Excellent”.

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