Software Development Manager

Plymouth Rock Assurance • Boston, MA

4d • $147 - $191

About The Position

We are 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. 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”.

Requirements

• 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.
• 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) Microservices architectures, REST APIs, GraphQL, and event-driven systems (Kafka, SNS/SQS, Pulsar)
• 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) Monitoring and observability platforms
• Hands-on experience with modern SDLC practices, including trunk-based development, feature flags, automated testing (JUnit, Cypress, Playwright), and code quality tooling.
• Demonstrated ability to manage resource planning, risk mitigation, stakeholder communication, and delivery for complex, high-visibility initiatives.
• Proven track record of partnering with architects, product owners, analysts, and project managers to estimate and deliver end-to-end system solutions.
• Excellent written and verbal communication skills.

Nice To Haves

• Experience in the insurance or financial services industry is a plus.

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.
• Recruit, mentor, and develop engineering talent, fostering a culture of innovation, accountability, and ownership.
• 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.
• Plan releases, manage backlogs, and coordinate cross-team dependencies to ensure predictable, on-time delivery.
• Manage staffing and resource allocation to balance workloads while optimizing team productivity and morale.
• Ensure high-quality delivery through strong engineering practices, CI/CD pipelines, automated testing, and DevSecOps principles.
• Collaborate closely with engineering, architecture, QA, product, and operations teams on complex, multi-team initiatives.
• Support the career growth of direct reports through regular coaching, feedback, and development planning.
• Maintain clear, transparent communication with stakeholders throughout the development lifecycle, supported by data and metrics.

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

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Number of Employees: 501-1,000 employees