Job Description

We are seeking a Director of Quality Assurance to lead the transformation of our QA organization into a modern, automation-first quality engineering function. This role will drive the strategy, execution and continuous improvement of testing practices across customer-facing and internal insurance platforms, ensuring high-quality, scalable, and reliable software delivery. The ideal candidate brings a strong track record of building and scaling test automation, improving engineering quality practices, and leading high-performing teams in an Agile environment.

Responsibilities

• Build, mentor, and lead a high-performing QA organization, including automation engineers and manual testers.
• Evolve team structure and skillsets to support increased automation and engineering maturity.
• Foster a culture of accountability, continuous learning, and quality ownership across teams.
• Communicate quality status, risks, and progress to executive leadership using clear metrics and insights.
• Define and execute a multi-year QA transformation strategy, shifting from manual-heavy testing to scalable, automation-first quality engineering practices.
• Establish a clear vision for quality across the SDLC, including test automation, shift-left testing, and continuous quality practices.
• Introduce and track quality metrics (e.g., defect escape rate, automation coverage etc) to drive data-informed decisions.
• Lead the design and implementation of robust test automation frameworks across UI, API, and backend systems.
• Champion modern testing practices, including CI/CD-integrated automation and test data management.
• Evaluate and implement tools and frameworks to improve automation scalability, reliability, and maintainability.
• Oversee test planning, execution, and release readiness for complex, customer-facing and internal applications.
• Ensure alignment between QA, engineering and product teams to deliver high-quality software on predictable timelines.
• Identify and mitigate risks related to quality, performance, and system reliability.
• Ensure quality practices support critical insurance workflows, including quoting, policy lifecycle, billing, and claims.

Qualifications

• 12+ years of experience in software quality assurance, with 5+ years in a leadership role managing QA or Quality Engineering teams.
• Proven track record of leading QA transformations, particularly moving from manual testing to scalable automation.
• Experience delivering quality for complex, customer-facing applications in Agile environments.
• Experience in insurance or financial services is strongly preferred.
• Deep expertise in test automation strategies, frameworks, and tools across UI, API, and backend layers.
• Hands-on experience with modern automation tools (e.g., Selenium, Cypress, Playwright, REST Assured, Karate, or similar).
• Strong understanding of CI/CD integration for automated.
• Familiarity with modern application architectures, including microservices, APIs, and event-driven systems.
• Proven ability to define and track KPIs to improve quality and delivery outcomes.
• Excellent communication and stakeholder management skills, with the ability to influence at all levels of the organization.

Perks and Benefits:

• 4 weeks accrued paid time off + 9 paid national holidays per year
• Free onsite gym at our Boston Location
• Tuition Reimbursement
• Low cost and excellent coverage health insurance options that start on Day 1 (medical, dental, vision)
• Robust health and wellness program and fitness reimbursements
• Auto and home insurance discounts
• Matching gift opportunities
• Annual 401(k) Employer Contribution (up to 7.5% of your base salary)
• Various Paid Family leave options including Paid Parental Leave
• Resources to promote Professional Development (LinkedIn Learning and licensure assistance)
• Convenient location directly across from South Station and Pre-Tax Commuter Benefits

The pay range for this position is $155,000 to $205,000 annually. 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 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”

#LI-SM1