Director, Cloud Platform & Automation Leader

Plymouth Rock Assurance; Boston (MA); Hybrid; USD 171,000 - 227,000; Full time

Job summary

Plymouth Rock Assurance is seeking a senior leader to drive design, engineering, and evolution of cloud platforms, modernizing, standardizing, and delivering scalable services. The role focuses on cloud-first, automation-driven operations and secure, cost-efficient platforms that accelerate application delivery and business outcomes.

The ideal candidate will guide managers/senior teams across infrastructure service delivery in a hybrid environment, shape roadmaps, manage budgets, and partner

Qualifications

• 8+ years leading infrastructure, operations, or cloud engineering teams.
• Experience managing managers or senior technical teams.
• Experience with hybrid environments and multiple clouds.
• Bachelor’s degree; MBA preferred.

Responsibilities

• Set direction for the Cloud Engineering function and governance.
• Own service delivery outcomes including velocity, availability, reliability, and security.
• Lead AWS migration and modernization strategy.
• Partner with execs to align infrastructure with business priorities.
• Represent cloud function in executive forums and audits.
• Sponsor modernization, automation, and debt reduction initiatives.

Skills

Leadership

Budget management

Cloud strategy

Hybrid infrastructure

Security collaboration

Agile delivery

Education

Bachelor’s degree

Master’s degree

Tools

AWS

Azure

GCP

Kubernetes

CI/CD

ITIL

Job description

Plymouth Rock Assurance is seeking a senior leader to drive design, engineering, and evolution of cloud platforms, modernizing, standardizing, and delivering scalable services. The role focuses on cloud-first, automation-driven operations and secure, cost-efficient platforms that accelerate application delivery and business outcomes.

The ideal candidate will guide managers/senior teams across infrastructure service delivery in a hybrid environment, shape roadmaps, manage budgets, and partner