eServices Software Development Manager

In this role, you will report to the Director of Application Development and will lead the design, delivery, and evolution of modern, cloud-native applications on AWS while building and mentoring high-performing engineering teams. This role is focused on strong technical leadership, execution excellence, and scalable system design in a fast-paced environment. Additionally, you will collaborate with cross-functional teams to identify opportunities for innovation and develop cutting-edge software solutions.

Responsibilities:

• Provide strong technical leadership to a team of software engineers building and maintaining scalable, customer-facing applications and digital platforms.
• Maintain transparent communication with stakeholders, providing regular updates backed by data and insights.
• Provide guidance and mentorship to team members, fostering skill development, and professional growth.
• Own and guide architectural decisions, promoting AWS-based, cloud-native design principles for resilience, scalability, and security.
• Oversee the analysis of complex business challenges and direct the development of innovative software solutions leveraging cutting-edge technologies. Drive engineering excellence through improvements in code quality, observability, CI/CD automation, and development best practices.
• Approve and guide the design and implementation of proof-of-concept projects to validate the feasibility and value of emerging technologies. Lead end-to-end delivery of software initiatives, including planning, estimation, execution, and release management.
• Serve as the primary liaison between technical teams and business stakeholders, ensuring alignment between technical capabilities and organizational goals. Recruit, mentor, and develop engineering talent, fostering a culture of accountability, ownership, and continuous learning.
• Manage team capacity, staffing, and resource allocation to balance short-term delivery goals with long-term sustainability.
• Facilitate collaboration between cross-functional teams to foster innovation and ensure successful implementation of new technologies into existing applications and systems. Collaborate with product, architecture, QA, and operations teams to deliver complex, cross-functional initiatives.
• Champion a culture of continuous improvement by encouraging creative problem-solving and the exploration of emerging industry trends. Track and communicate progress using Agile methodologies, KPIs, and engineering metrics.
• Ensure high-quality delivery through automated testing, DevSecOps practices, and well-defined SDLC processes.
• Monitor and evaluate project progress to ensure timely delivery and alignment with organizational objectives. Identify risks, resolve technical challenges, and ensure alignment with business objectives and technical strategy.
• Support career growth of direct reports through coaching, performance feedback, and development planning.

Qualifications:

• Bachelor's degree in computer science or related field with 10+ years of experience in building commercial software systems.
• 3+ years of experience leading engineering teams in an Agile environment.
• Strong background in designing and building distributed, cloud-native systems on AWS (experience with services such as API Gateway, Lambda, ECS/EKS, S3, RDS/DynamoDB is preferred).
• Proven experience in software development, with a strong foundation in programming languages such as Python, Java, or C++.
• Expertise in JVM-based technologies: Java, Spring Boot, Spring Cloud.
• Experience with microservices architectures, REST APIs, GraphQL, and event-driven systems (Kafka, SNS/SQS, Pulsar).
• Experience applying emerging technologies to solve complex business problems and drive innovation. Solid knowledge of modern SDLC practices, including automated testing, trunk-based development, and feature flags.
• Experience with agile development methodologies and rapid prototyping techniques Ability to thrive in a fast-paced, dynamic environment and adapt to changing priorities.
• Strong hands-on experience with containerization and orchestration using Docker and Kubernetes.
• Proficient with cloud platforms such as AWS, Azure, or Google Cloud Platform. Familiarity with modern front-end technologies such as React, Angular, TypeScript, or similar frameworks.
• Demonstrated ability to foster creativity, help teams generate ideas and new ways of doing business. Skilled relationship-builder and cross-functional collaborator with proven leadership and teamwork abilities, able to manage priorities and drive results across all stakeholders.
• Experience building and leading high performing teams.
• Strong written and verbal communication skills, including proven ability to communicate with technical and non-technical audiences.
• Proven ability to manage delivery, stakeholder communication, and risk for complex initiatives.
• Strong technical and project management skills.
• Experience with CI/CD pipelines (GitHub Actions, Jenkins, GitLab CI, or similar).
• Advanced application architecture design experience and prior exposure to multiple SDLC's.Proficiency in Infrastructure as Code (Terraform, CloudFormation) and strong understanding of DevSecOps practices and tools (SonarQube, Veracode, or similar code quality and security platforms).
• Prior exposure to distributed application performance engineering, cloud computing, social media programs, mobile application development, database design concepts, middleware concepts, user interface development, and information security engineering.
• Knowledge of Property & Casualty industry best practices would be a plus.

Technical Qualifications:

• Strong background in designing and building distributed, cloud-native systems on AWS (experience with services such as API Gateway, Lambda, ECS/EKS, S3, RDS/DynamoDB is preferred).
• Expertise in JVM-based technologies: Java, Spring Boot, Spring Cloud.
• Experience with microservices architectures, REST APIs, GraphQL, and event-driven systems (Kafka, SNS/SQS, Pulsar).
• Familiarity with modern front-end technologies such as React, Angular, TypeScript, or similar frameworks.
• Strong hands-on experience with containerization and orchestration using Docker and Kubernetes.
• Experienced in leveraging cloud platforms such as AWS, Google Cloud, or Azure to deploy and manage AI models at scale. Hands-on experience with containerization technologies like Kubernetes and Docker. Experience with CI/CD pipelines (GitHub Actions, Jenkins, GitLab CI, or similar) and Infrastructure as Code (Terraform, CloudFormation).
• Proficiency with Jira, Maven, JUnit, Nexus, Hudson, Sonar, and modern DevOps practices. Experience with IaC tools such as Terraform, CloudFormation, and CI/CD automation. Strong understanding of DevSecOps practices and tools (SonarQube, Veracode, or similar code quality and security platforms).
• Experience with observability and monitoring tools (CloudWatch, Prometheus, Grafana, ELK, etc.).
• Solid knowledge of modern SDLC practices, including automated testing, trunk-based development, and feature flags.
• Experience with project management tools like Jira for Agile planning, tracking, and reporting. Exposure to AI/ML or LLM-based systems is beneficial.
• Experience working with both relational and non-relational databases, including PostgreSQL, DynamoDB, DocumentDB, MongoDB, MS SQL Server, and Snowflake.

The pay range for this position is $151,000 to $198,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.

Perks and Benefits:

• 4 weeks accrued paid time off, 8 paid national holidays per year, and 2 floating holidays
• Low cost and excellent coverage health insurance options that start on Day 1 (medical, dental, vision)
• Annual 401(k) Employer Contribution
• Free onsite gym and health center at our Woodbridge Location
• Resources to promote Professional Development (LinkedIn Learning and licensure assistance)
• Robust health and wellness program and fitness reimbursements
• Various Paid Family leave options including Paid Parental Leave
• Tuition Reimbursement

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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