Director of Cloud Engineering

In this role, you will lead the design, engineering, and evolution of Plymouth Rock’s cloud platforms, with a primary focus on enabling modernization, standardization, and scalable platform capabilities. You will drive the transition to a cloud-first, automation-driven operating model, delivering secure, cost-efficient, and highly reusable services that accelerate application delivery and business outcomes.

The ideal candidate will have recent experience leading managers and senior technical teams responsible for all aspects of infrastructure service delivery in a hybrid environment. This role requires the ability to set strategy, translate it into roadmaps, manage budgets and vendor relationships, develop leadership talent, sponsor transformation, and guide teams designing and delivering reliable, secure, and cost-effective services.

Essential Functions and Responsibilities:

• Set the direction for the Cloud Engineering function, including organizational priorities, operating model, service ownership, engineering standards, and delivery expectations.
• Own organizational design, workforce planning, leadership development, succession planning, and talent pipeline development for the function.
• Own service delivery outcomes and metrics across the function, including (but not limited to) delivery velocity, service availability, reliability, operational resilience, incident trends, MTTR, change success rate, patch compliance, backup success, capacity utilization, cloud spend variance, KPI performance, and stakeholder satisfaction.
• Drive the planning, design, and execution of the AWS migration and modernization strategy, with a focus on secure architecture, reusable engineering patterns, operational readiness, and alignment with business priorities.
• Ensure the resilience, performance, and availability of systems, including participation in off-hours escalation when major incidents require leadership support.
• Maintain a forward-looking view of cloud, automation, security, and operations practices, and apply that perspective to roadmap planning, modernization decisions, and platform standards.
• Partner with Technology and business leaders to understand business needs, shape infrastructure priorities, and deliver cost-effective technology services across cloud, systems, storage, network, security, and related platforms.
• Own cloud security posture in partnership with CISO, Corporate Security, GRC, and Architecture, including vulnerability management governance, audit readiness, regulatory compliance, secure architecture, and risk-based remediation priorities.
• Participate as an integral member of the infrastructure management team, setting platform strategy, service portfolio governance, investment recommendations, CapEx and OpEx planning, policy decisions, risk trade-offs, and continuous improvement priorities.
• Sponsor modernization, automation, tooling, and technical debt reduction initiatives that improve reliability, reduce operational toil, improve employee productivity, and support long-term business outcomes.
• Lead disciplined change management, delivery tracking, cross-team coordination, and stakeholder communication for cloud engineering initiatives, ensuring dependencies, risks, decisions, and execution status are visible and actively managed.
• Establish service level objectives for the function and ensure they are communicated, measured, and met.
• Manage strategic vendor, managed service provider, cloud provider, and software partner relationships, including performance, escalation, renewal input, contract support, and investment recommendations.
• Represent the cloud function in executive forums, major incident reviews, vendor discussions, audit conversations, and enterprise planning discussions.

Qualifications and Education:

• 8+ years of progressive experience leading infrastructure, operations, platform, or cloud engineering teams in an enterprise environment.
• Experience managing managers or senior technical teams, including hiring, performance management, coaching, workforce planning, and succession planning.
• Experience managing off-shore resources
• Strong technical understanding of public and private cloud platforms and services. AWS experience is preferred; Azure or GCP experience is beneficial.
• Demonstrated experience setting technology roadmaps, governance practices, operating models, and investment recommendations.
• Experience leading transformation, modernization, automation, technical debt reduction, or cloud migration programs.
• Experience presenting to senior executives and translating technical, operational, financial, and risk topics into business terms.
• Experience with hybrid infrastructure environments, including Windows, Linux, Active Directory, virtualization, storage, networking, databases, middleware, Kubernetes, and cloud-native services.
• Strong understanding of infrastructure as code, CI/CD, automation, source control, configuration management, monitoring, logging, and operational support practices.
• Experience with ITIL-aligned practices, including change management, incident management, problem management, service transition, operational controls, and production support governance.
• Experience with agile delivery practices, including sprint planning, backlog prioritization, iterative delivery, dependency tracking, cross-team coordination, and delivery transparency across engineering, operations, security, and application teams.
• Practical experience with disaster recovery, backup and recovery, business continuity planning, incident response, IT service management, and production support for critical systems specifically in hybrid environments.
• Experience managing budgets, cloud consumption, vendor relationships, service providers, contracts, and technology investment recommendations.
• Experience partnering with security, risk, compliance, and audit teams to address vulnerability management, patching, access controls, logging, encryption, and regulatory requirements.
• Strong critical thinking, decision making, and problem-solving skills.
• Bachelor’s degree in relevant field of study is required; Master’s or MBA preferred.

Salary Range: $171,000 to $227,000 per year + bonus. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.

About the Company:

The Plymouth Rock Company and its affiliated group of companies write and manage over $2.2 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 2,000 people and is headquartered in Boston, Massachusetts. Plymouth Rock Assurance Corporation holds an A.M. Best rating of “A-/Excellent”.

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