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Plymouth Rock Assurance · 20 hours ago

Software Development Manager

Boston, MA

Full-time

Onsite

Director/Executive

$147K/yr - $191K/yr

10+ years exp

Plymouth Rock Assurance is a well-established insurance company that writes and manages over $2 billion in personal and commercial insurance. They are seeking an experienced Software Development Manager to lead the design and delivery of cloud-native applications while mentoring engineering teams and ensuring high-quality delivery through strong engineering practices.

Auto InsuranceFinancial ServicesInsurance

H1B Sponsor Likely

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

Qualification

Cloud-native applicationsAgile developmentJVM-based technology stacksMicroservices architecturesCI/CD pipelinesDockerKubernetesInfrastructure as CodeAutomated testingStakeholder communicationCommunication skillsMentoring

Required

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

Preferred

Experience in the insurance or financial services industry is a plus

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

Company

Plymouth Rock Assurance

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Founded in 2001

Boston, Massachusetts, USA

1001-5000 employees

https://www.plymouthrock.com

H1B Sponsorship

Plymouth Rock Assurance has a track record of offering H1B sponsorships. Please note that this does not guarantee sponsorship for this specific role. Below presents additional info for your reference. (Data Powered by US Department of Labor)

Distribution of Different Job Fields Receiving Sponsorship

Represents job field similar to this job

Trends of Total Sponsorships

2025 (8)

2024 (12)

2023 (6)

2022 (7)

2021 (5)

2020 (12)