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EServices Software Development Manager

Job in Boston, Suffolk County, Massachusetts, 02298, USA
Listing for: Plymouth Rock Assurance
Full Time position
Listed on 2026-05-15
Job specializations:
  • Software Development
    Cloud Engineer - Software, Software Engineer, Full Stack Developer, DevOps
Salary/Wage Range or Industry Benchmark: 80000 - 100000 USD Yearly USD 80000.00 100000.00 YEAR
Job Description & How to Apply Below

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, Dev Sec Ops  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/Dynamo

    DB 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, Graph

    QL, 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, Type Script, 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 (Git Hub Actions, Jenkins, Git Lab CI, or similar).
  • Advanced application architecture…
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