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Plymouth Rock Assurance Logo

Software Development Manager

Plymouth Rock Assurance

$147,000 - $191,000
Dec 30, 2025
Boston, MA, US
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The Plymouth Rock Company is seeking an experienced Software Development Manager to lead the design, delivery, and evolution of modern, cloud-native applications while building and mentoring high-performing engineering teams.

Requirements

  • Proven experience designing and building cloud-native, distributed systems on platforms such as AWS, Azure, or GCP.
  • Strong expertise in modern JVM-based technology stacks, including Java, Spring Boot / Spring Cloud (Kotlin a plus)
  • Experience with modern web frameworks and front-end technologies: Angular, React, TypeScript, Next.js, CSS-in-JS, and design systems
  • Broad experience with modern development tools and platforms, including Docker, Kubernetes, and container orchestration
  • CI/CD pipelines (GitHub Actions, GitLab CI, Jenkins, Argo CD, Harness)
  • Infrastructure as Code (Terraform, CloudFormation)
  • Security and DevSecOps tools (Snyk, Veracode, SonarQube)

Responsibilities

  • Provide strong technical leadership to a team of high-performing software engineers building and maintaining modern, customer-facing applications and digital experiences.
  • Own and guide technical architecture decisions, championing cloud-native design principles to deliver scalable, resilient, and secure software platforms.
  • Drive continuous improvement in code quality, observability, automation, and development workflows using metrics and data-driven insights.
  • Ensure high-quality delivery through strong engineering practices, CI/CD pipelines, automated testing, and DevSecOps principles.
  • Plan releases, manage backlogs, and coordinate cross-team dependencies to ensure predictable, on-time delivery.
  • Deliver accurate estimates and feasibility assessments for new initiatives, ensuring alignment with business goals and technical strategy.
  • Track, measure, and communicate progress against key milestones using Agile planning tools and engineering KPIs.

Other

  • Bachelor's degree in Computer Science or a related field, with 10+ years of experience building commercial software systems.
  • 3+ years of experience leading engineering teams in an Agile development environment.
  • Excellent written and verbal communication skills.
  • Experience in the insurance or financial services industry is a plus.
  • Demonstrated ability to manage resource planning, risk mitigation, stakeholder communication, and delivery for complex, high-visibility initiatives.