Software Development Manager – Core Application Team

Role Overview:

The Manager will lead a team responsible for the development, maintenance, and enhancement of our Policy and Billing Administration System. This role ensures delivery of high-quality technology solutions aligned with business objectives, regulatory requirements, and customer needs.

Essential Functions and Responsibilities:

Team Leadership & Management

  • Lead and mentor a team of Systems Analysts.
  • Foster a collaborative, high-performance culture focused on innovation and continuous improvement.

Application Development & Maintenance

  • Oversee design, development, and deployment of core applications supporting underwriting, rating, policy issuance, billing, and claims.
  • Ensure adherence to architectural standards, security protocols, and compliance requirements.

Project Delivery

  • Manage end-to-end delivery of projects, including planning, resource allocation, and risk management.
  • Collaborate with business stakeholders to define requirements and prioritize enhancements.

Vendor & Platform Management

  • Coordinate with third-party vendors for platform upgrades and integrations.
  • Monitor SLAs and ensure optimal performance of vendor-supported applications.

Operational Excellence

  • Implement best practices for application lifecycle management, including DevOps, CI/CD, and automated testing.
  • Track KPIs for system performance, defect resolution, and team productivity.

Performance Metrics:

  • On-time delivery of projects.
  • Reduction in application defects and downtime.
  • Team engagement and retention.
  • Successful implementation of strategic initiatives (e.g., modernization, automation).

Qualifications and Education:

  • Bachelor’s degree in computer science, information systems, or related field.
  • 5+ years of experience in IT leadership roles within Property & Casualty insurance domain.
  • Strong knowledge of P&C insurance processes (Policy, Billing, Claims).
  • Hands-on experience with core insurance platforms Policy Pro, Billing Pro, claims Pro preferred.
  • Proficiency in project management methodologies (Agile/Scrum).
  • Excellent communication and stakeholder management skills.
  • Skilled in cloud migration and modern architecture.
  • Familiarity with regulatory compliance in insurance (e.g., state filings, data privacy).
  • Knowledge of integration tools and document management systems (e.g., OpenText xPression).

Salary Range: $135,000-$188,000 per year. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.

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”.

#LI-DNI

About Plymouth Rock Assurance

If you’ve found your way to our LinkedIn page, you’re likely here for one of two reasons: You’re reviewing insurance companies or you’re browsing new career opportunities. Well, you’ve come to the right place. Insurance Customer In its 40 years, Plymouth Rock Assurance has grown to be one of the leading auto and home insurers in the Northeast. With unique features like Crashbusters® mobile claims vans, Door to Door Valet Claim Service®, the Get Home Safe® taxi and rideshare benefit, Road Rewards® and our Home Insurance Quick Quote, we’re committed to delivering our customers “More Than Just Insurance.” To get a free quote, visit plymouthrock.com or talk to a Plymouth Rock agent. Job Seeker We take pride in both the strength and commitment of our Plymouth Rock Assurance team. We actively seek individuals who exhibit friendliness, integrity, loyalty, hard work and the pursuit of excellence. If you’re currently looking for a new employment opportunity, we hope you’ll consider Plymouth Rock. For a full list of job openings, please visit www.plymouthrock.com/about/careers.

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