As specialty insurers accelerate digital transformation and data-driven underwriting, Chubb has announced a leadership transition within Westchester, its North American wholesale excess and surplus (E&S) insurance business. The company has appointed Dave Roberts as Vice President, Chubb Group and Division President of Westchester, while longtime executive Dave Lupica assumes the newly created role of Executive Chairman, supporting governance and long-term strategic direction.

The excess and surplus (E&S) insurance market continues to expand as businesses face increasingly complex risks ranging from cyber threats and climate events to emerging technologies and evolving regulatory requirements. Against this backdrop, Chubb has announced executive leadership changes designed to strengthen the long-term growth of its Westchester wholesale specialty insurance business.

Effective immediately, Dave Roberts succeeds Dave Lupica as Vice President, Chubb Group and Division President of Westchester. Lupica has transitioned to Executive Chairman, where he will provide governance oversight and strategic guidance for Chubb’s North American wholesale E&S operations.

The appointments reflect Chubb’s continued investment in specialty insurance capabilities as insurers increasingly combine underwriting expertise with advanced analytics, automation, and digital platforms to improve risk assessment and operational efficiency.

Leadership Transition Supports Next Phase of Growth

In his new role, Roberts will oversee Westchester’s wholesale E&S business across North America, leading the delivery of specialty insurance products through wholesale broker partners.

Roberts has served as Chief Operating Officer of Westchester since 2025 and previously led several strategic initiatives, including digital transformation, middle-market operations, underwriting performance, and small business insurance programs. He will report to Scott Meyer, Senior Vice President, Chubb Group and Chief Operating Officer of North America Insurance.

“Dave is an underwriter at his core, with a disciplined approach to evaluating risk from every angle,” said Juan Luis Ortega, Executive Vice President, Chubb Group and President of North America Insurance. “He believes that combining underwriting expertise with data analytics leads to better decision making, from assessing individual risks to portfolio management.”

The emphasis on analytics reflects a broader industry shift toward technology-enabled underwriting, where insurers increasingly leverage artificial intelligence, predictive modeling, and alternative data to enhance pricing accuracy and portfolio management.

Executive Chairman Role Focuses on Strategy

Lupica’s transition follows more than 26 years of leadership at Chubb, where he played a central role in expanding several business lines, including Financial Lines, Commercial Risk Services, and Westchester.

During his tenure, he also helped lead Westchester’s digital transformation initiatives and supported the growth of Healthy Paws, Chubb’s pet insurance business.

His contributions to the specialty insurance market were recognized in 2024 with induction into the Insurance Business America Hall of Fame.

According to Scott Meyer, Lupica helped position Westchester as a leading player in the wholesale E&S market while emphasizing disciplined underwriting and leadership development.

Technology Is Reshaping Specialty Insurance

The executive appointments come as specialty insurers modernize underwriting operations through automation, cloud computing, artificial intelligence, and advanced data analytics.

Historically, E&S insurance has relied heavily on experienced underwriters evaluating complex or non-standard risks that fall outside traditional insurance markets. Today, insurers increasingly augment those decisions with predictive analytics, machine learning models, and digital workflow platforms that improve speed, consistency, and portfolio insights without replacing human underwriting judgment.

Roberts has previously overseen Westchester’s digital initiatives, positioning him to continue integrating technology into underwriting operations while maintaining the company’s specialty expertise.

Across the broader insurance industry, technology companies including Microsoft, Amazon Web Services (AWS), Google Cloud, Salesforce, Adobe, and NVIDIA are providing AI infrastructure, cloud platforms, customer engagement tools, and analytics capabilities that support insurers’ digital modernization efforts.

Applications include automated policy processing, intelligent document analysis, fraud detection, catastrophe modeling, claims automation, and AI-assisted underwriting.

The E&S Market Continues to Expand

The wholesale E&S market has experienced sustained growth in recent years as businesses seek coverage for increasingly complex exposures, including cyber insurance, environmental liabilities, professional risks, and emerging technology sectors.

According to AM Best, the U.S. excess and surplus insurance market has consistently outpaced the broader property and casualty industry in premium growth. Deloitte also identifies AI, predictive analytics, and digital underwriting as key priorities for insurers seeking operational efficiency and improved customer experiences.

For Chubb, the leadership transition represents continuity rather than a strategic shift. Lupica remains involved in governance and long-term planning, while Roberts brings operational experience and digital expertise to oversee day-to-day execution.

As specialty insurance becomes increasingly data-driven, insurers that successfully combine experienced underwriting with intelligent analytics platforms are expected to strengthen risk selection, improve operational performance, and respond more effectively to rapidly changing market conditions.

Market Landscape

The global insurance industry is accelerating investments in AI, cloud computing, predictive analytics, and intelligent underwriting platforms to improve risk evaluation and operational efficiency. Specialty insurers are particularly focused on digital capabilities that support complex commercial risks requiring expert human judgment alongside advanced data analysis.

According to Deloitte, digital underwriting and AI are transforming insurance operating models, while AM Best reports continued growth in the U.S. excess and surplus insurance market as organizations seek specialized coverage for emerging risks.

Top Insights

• Chubb has promoted Dave Roberts to lead Westchester while Dave Lupica transitions to Executive Chairman, ensuring continuity in the company’s specialty insurance strategy.
• The leadership changes reinforce Westchester’s focus on combining underwriting expertise with advanced data analytics and digital capabilities.
• AI-powered underwriting and predictive analytics are becoming strategic priorities across the excess and surplus insurance market.
• Technology investments are helping specialty insurers improve pricing accuracy, operational efficiency, and portfolio management for increasingly complex commercial risks.
• Continued growth in the E&S market is driving demand for digital insurance platforms that support both brokers and enterprise customers.

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