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Plymouth Rock Assurance Corporation

Director of Infrastructure Operations

Plymouth Rock Assurance Corporation, Boston, MA


Director of Infrastructure Operations

In this position, you will lead several teams responsible for the design, engineering, operational support, and strategic modernization of the computer services that serve as the foundation for all the firm's hybrid cloud infrastructure.

The ideal candidate will have recent experience leading teams that build and support infrastructure as a service using hybrid cloud solutions such as Amazon Web Services and VMWare and be able to collaborate closely with the other members of the organization to modernize the way we provision and manage infrastructure services. This person will be familiar with Windows and Linux Operating systems, infrastructure as code, and building solutions to meet the needs of their customers.

Essential Functions and Responsibilities:
  • The role oversees and manages the following teams: Windows and Linux System Admins, Storage and Datacenter, Database Administration, Middleware, Change Management, Disaster Recovery, and a 24/7 Operations Team.
  • This is not expected to be a hand on role, but the selected candidate will be expected to provide technical mentorship and guidance to the members of the team and as such should bring a strong technical aptitude based on a career history in working in hands on technical roles.
  • Brings current IT knowledge, future vision, leadership and management abilities, process design skills and business expertise to transform the Infrastructure and Operations function in on premise and a hybrid cloud environment (AWS, IAAS, PAAS, SAAS, AZURE, GCP).
  • Works closely with the management team and other key business decision-makers in identifying and implementing cost-effective IT infrastructure technology solutions for all aspects of the business inclusive of infrastructure, software, hardware, networks, security that enhance mission critical operations of the IT department for Plymouth Rock companies.
  • In charge of Business Continuity and Disaster Recovery within the organization as well as the recommendation and implementation of new investments within the technology infrastructure ensuring proper configuration, implementation, maintenance, and monitoring, sites/software, servers, data and data encryption, and internet connections.
  • Leads the team members in the analysis, enhancement, and tailoring of current practices, processes and existing systems with a goal of increasing operating efficiency as well as reduce and cut costs within the business where appropriate.
  • Work with the CISO to develop a secure architecture and implement procedures and controls that ensure that information and data are secure and in compliance with the security and storage regulations of the business.
  • Builds a collaborative culture within the department and partners with various departments within the organization to gather feedback and develop insights that will lead to the improvement of IT services.
  • Participate as an integral member of the IT management team responsible for defining and implementing software technology strategy, CapEx and OpEx plans and continuous improvement objectives.
  • In this capacity, the role also plays a mentorship role to key IT Teams, promoting their professional growth.
  • Introduces innovative, differentiating infrastructure and operations capabilities that enhance our overall competitive capabilities and enhance employees' productivity.
  • Works with the IT leadership team on the service portfolio and governance required to prioritize resources, including budget.
  • Builds successful stakeholder relationships with other IT and business leaders by developing a clear understanding of business needs, acting as a trusted advisor, and ensuring cost-effective delivery of IT services to meet those needs.
  • Collaborates with the Corporate Security Team to ensure IT Operations and Security embrace and apply security strategy.
  • Establishes service level objectives for IT Operations and Security and ensures they are communicated, executed, and met.
  • Ensure the resilience, performance, and availability of our Tier 0/Tier 1 systems, which may require off-hours support during incidents
  • Experience planning and managing financial budgets.
  • Manage Capacity Planning strategies for the technologies under their remit including system resource planning, license management and cloud resource planning.


Qualifications and Education:
  • 8+ years of experience managing infrastructure engineering teams.
  • Strong technical understanding of public/private cloud platforms and services (Amazon Web Services (AWS) preferred but experience with other providers such as Azure and GCP is beneficial) ).
  • Experience with Virtualization technologies, such as VMWare.
  • Experience with Redhat JBoss, IBM AIX, IBM WebSphere, Kubernetes, Microsoft Windows, Active Directory (AD), AWS RDS, MySQL, non-relational DBs; Doc DB, DynamoDB, Redis, Replication strategies such as AWS DMS and SQL replication.
  • Knowledge of storage and storage platforms such as; Dell, AWS S3, EFS, AWS FSXn (NetApp), Celerra Replicator, and Dell RecoverPoint.
  • Strong technical understanding of application, network, & cloud security services.
  • Strong understanding and experience with CI/CD and Infrastructure as Code concepts.
  • Strong critical thinking, decision making, and problem-solving skills.


About the Company:

The Plymouth Rock Company and its affiliated group of companies write and manage over $2.0 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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