Job Description

We are seeking an experienced Software Development Manager to lead the design, delivery, and evolution of modern, cloud-native applications while building and mentoring a high-performing engineering team.

Responsibilities

• Provide strong technical leadership to a team of high-performing software engineers building and maintaining modern internal applications.
• 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
• 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 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.

Qualifications

• 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
• Proven experience designing and building cloud-native, distributed systems on platforms such as AWS or Azure.
• Strong expertise in modern technology stacks, including:
• Microsoft .NET environment, Visual Studio, IIS, Team Foundation Server, HTML, JavaScript, JSON, XML, SOAP
• Working knowledge of Java full stack development
• Microservices architectures, REST APIs and event-driven systems
• Angular UI development
• Strong expertise on major database platforms
• SQL Server stored procedure development, debugging and tuning
• DB2 experience is a plus
• Snowflake experience is a plus
• Hands-on experience with modern SDLC practices, including trunk-based development, feature flags, automated testing (JUnit), 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.
• Experience in the insurance or financial services industry is a plus.

Salary Range: The pay range for this position is $151,500 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 & 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 $2.2 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 2,000 people and is headquartered in Boston, Massachusetts. Plymouth Rock Assurance Corporation holds an A.M. Best rating of “A-/Excellent”.

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