Chubb, a global insurer offering commercial and personal property and casualty insurance, accident and health insurance, reinsurance and life insurance products and services, has announced changes to the senior leadership team at Westchester, its North American wholesale excess and surplus (E&S) lines business.
Dave Lupica, Vice President, Chubb Group and Division President, Westchester, has moved into the role of Executive Chairman. Dave Roberts, who has served as Chief Operating Officer of Westchester, has been appointed Vice President, Chubb Group and Division President, Westchester, taking over from Lupica. The appointments took effect immediately, according to Chubb.
In his new position, Lupica will continue to support Westchester by providing governance oversight and strategic guidance for the company’s wholesale E&S operations across North America. Chubb highlighted Lupica’s long tenure with the business, noting his role in several areas of expansion and development during his 26 years with the company.
Lupica was involved in establishing its Financial Lines practice, launching the company’s first Small Business division within Commercial Risk Services, overseeing Westchester’s digital transformation and expanding Healthy Paws into a significant pet insurance provider. His contribution to the excess and surplus market was recognised in 2024 when he was inducted into the Insurance Business America Hall of Fame.
Roberts will assume responsibility for the day-to-day executive leadership of Chubb’s North American wholesale E&S lines business, with a focus on delivering Westchester’s specialist products and services to wholesale brokers. Roberts will report to Scott Meyer, Senior Vice President, Chubb Group and Chief Operating Officer, North America Insurance.
“Under Dave Lupica’s leadership, Westchester has grown with discipline and strengthened its position as a leader in wholesale E&S,” commented Meyer. “Throughout his career at Chubb, Dave has consistently built strong businesses while investing in the development of those around him. I’m grateful for his partnership over the years and look forward to his continued contributions in this new role.”
Juan Luis Ortega, Executive Vice President, Chubb Group and President, North America Insurance, added: “Dave is an underwriter at his core, with a disciplined approach to evaluating risk from every angle. He believes that combining underwriting expertise with data analytics leads to better decision making, from assessing individual risks to portfolio management.”
Lupica brings more than four decades of insurance industry experience to his new role. He joined Chubb, then operating as ACE, in 2000 as Executive Vice President of ACE USA’s Professional Risk Division. He later held leadership positions including Division President of ACE Commercial Risk Services and Division President, ACE Westchester Professional Lines.
In 2016, he became Chief Operating Officer and Distribution Management Officer of Westchester, before being appointed Vice President, Chubb Group and Division President, Westchester, in 2024. Before joining ACE, Lupica held management roles with Starr Excess Liability Company Inc. of Bermuda, Alexander & Alexander (now Aon), and AIG. He holds a Bachelor of Arts degree from Hobart and William Smith Colleges.
Roberts has led Westchester as Chief Operating Officer since 2025, overseeing operations for the company’s wholesale E&S business in North America.
He has almost two decades of insurance industry experience and has spent more than 10 years with Westchester, where he previously held the roles of Executive Vice President, Head of Digital and Middle Market, and senior positions covering Small Business products, business development, underwriting operations and profitability performance. Roberts also holds a Bachelor of Science degree in Management from Penn State University.
