Managing Director of Operational Excellence - Plymouth Rock Assurance

The Managing Director of Operational Excellence will lead enterprise-wide process improvement efforts through reengineering and intelligent automation. This change agent will partner with business units to identify opportunities, design innovative solutions, implement recommendations, and measure outcomes to ensure sustainable improvements to both customer experience and efficiency.

This position oversees a high-performing team of process improvement professionals, including reengineering practitioners, data analysts, and change management experts. Together, the team is responsible for delivering measurable operational efficiencies, embedding continuous improvement practices across the organization, and fostering a culture of innovation.

Key Responsibilities

Process Optimization:

• Lead teams through all phases of reengineering initiatives, including discover, diagnose, design, implement, measure, and improve.
• Address all dimensions of improvement: people, process, technology, and policy.
• Utilize appropriate reengineering tools and methodologies to achieve results.
• Track and report on operational performance metrics for results achieved versus targets

Change Management:

• Drive change initiatives to ensure alignment with the company’s strategic objectives.
• Overcome resistance to change by addressing concerns and demonstrating the value of proposed solutions.
• Help embed new processes, systems, and tools within the organization.

Team Development:

• Inspire and manage a team of reengineering and intelligent automation specialists, fostering innovation, collaboration, and accountability.
• Ensure team is equipped with necessary skills, tools, and resources to achieve objectives.
• Promote professional growth through training, development, and knowledge sharing.
• Empower team members to translate ideas into actionable business results.

Collaboration & Stakeholder Relations:

• Build and maintain trusting relationships across the organization to ensure alignment, transparency, and collaboration.
• Partner with senior leadership to identify areas for operational improvement.
• Engage with cross-functional stakeholders to ensure alignment and effective implementation.

Required Expertise

• Bachelor’s degree in business administration, operations management, engineering, or related field; MBA or equivalent advanced degree preferred.
• 10+ years of experience in operational leadership roles, with a proven record of leading cross-business and cross-functional initiatives that deliver significant value.
• Proven expertise in Lean, Six Sigma, or similar methodologies.
• Strong analytical and problem-solving skills with focus on data-driven decision-making.
• Demonstrated ability to lead large initiatives and drive organizational transformation.
• Excellent interpersonal, communication, and leadership skills.
• Experience in insurance and/or consulting is a plus.
• Familiarity with Intelligent Automation tools, including RPA, IDP, AI/ML also a plus.
• Strategic thinking and planning.
• Strong financial and business acumen.
• Collaborative mindset with the ability to influence at all organizational levels.
• Commitment to fostering a culture of excellence and accountability.

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 AM Best rating of “A-/Excellent.”