Chubb Strengthens Leadership Team with Key Appointments at Westchester

Chubb, a leading name in the insurance industry, has recently made important executive appointments within Westchester, its wholesale excess and surplus (E&S) lines business in North America. On August 4, 2026, the company revealed that Dave Lupica will assume the role of Executive Chairman, while Dave Roberts has been promoted to Division President. Both appointments take effect immediately.

Key Leadership Roles

Lupica has an extensive history with Chubb, having served in various capacities over the last 26 years that contributed significantly to the company’s growth. His role as Executive Chairman will see him providing governance oversight and strategic guidance specifically for Chubb's wholesale E&S business. He has played a key role in numerous initiatives, including the establishment of Chubb's Financial Lines practice and pioneering the company’s first Small Business division within Commercial Risk Services. Additionally, he has led digital transformations at Westchester and helped grow Healthy Paws into a leading name in pet insurance.

His accomplishments in the E&S market were further validated when he was inducted into the Insurance Business America Hall of Fame in 2024, a testament to his influence and contributions to the sector.

On the other hand, Roberts, who previously held the role of Chief Operating Officer at Westchester, has been appointed as Vice President and Division President. His responsibilities will include overseeing Chubb’s wholesale E&S lines business and ensuring that Westchester continues to deliver specialized products tailored to the needs of wholesale brokers. He will report directly to Scott Meyer, the Senior Vice President of Chubb Group and Chief Operating Officer of North America Insurance.

Career Backgrounds

Throughout his career at Chubb, Lupica has consistently been recognized for building sustainable business practices while mentoring others within the company. Scott Meyer praised Lupica's leadership style, stating, “Under Dave Lupica's leadership, Westchester has grown with discipline and strengthened its position as a leader in wholesale E&S.”

Roberts brings nearly two decades of insurance industry experience, having dedicated more than ten years to Westchester itself. His background includes previous roles that positioned him strategically in different aspects of the company, such as overseeing the digital transition and heading the Middle Market division. He holds a Bachelor of Science degree in Management from Penn State University, which supports his analytical approach to risk assessment.

Looking Ahead

With these new appointments, Chubb aims to continue its legacy of leadership in the insurance market, adapting to new challenges and opportunities as they arise. The experience and expertise of both Lupica and Roberts is expected to play a pivotal role in navigating the evolving landscape of insurance and enhancing the service offerings of Westchester.

In summary, the leadership changes at Chubb’s Westchester mark a significant step forward in reinforcing the company’s commitment to innovation, growth, and excellence in the insurance sector. As the landscape of insurance evolves, Chubb is well-positioned to lead and adapt under this new leadership structure.

About Chubb

Chubb Limited (NYSE: CB) operates across 54 countries, providing a suite of commercial and personal insurance solutions. Its robust service offerings and exceptional financial strength define its standing as a global insurance leader, focused on meeting client needs through innovative products and strategies. With around 45,000 employees worldwide, Chubb remains dedicated to ensuring customer satisfaction and continued growth.