Westchester, a Chubb Company, Announces Key Leadership Appointments

Rhea-AI Summary

Chubb (NYSE: CB) announced leadership changes at Westchester, its wholesale excess and surplus (E&S) lines business in North America. Dave Lupica, previously Vice President, Chubb Group and Division President, Westchester, has been named Executive Chairman, focused on governance oversight and strategic advice for the wholesale E&S business.

Dave Roberts, formerly Chief Operating Officer, Westchester, has been appointed Vice President, Chubb Group and Division President, Westchester, succeeding Lupica. The appointments are effective immediately. According to Chubb, Lupica brings more than 40 years of industry experience, while Roberts has nearly 20 years of experience, including over a decade in senior roles at Westchester.

Positive

• Orderly leadership transition with Lupica moving to Executive Chairman and Roberts to Division President, effective immediately
• Deep experience retained, as Lupica brings 40+ years and Roberts nearly 20 years of insurance industry background
• Continuity at Westchester with Roberts promoted internally after serving as Chief Operating Officer of the business

Negative

• None.

News Explained

The immediate change is operational: Dave Roberts now has executive operating responsibility for Chubb’s North American wholesale E&S business, oversees delivery of its tailored specialty products to wholesale brokers, and reports to Scott Meyer.

AI-generated analysis. How Rhea-AI works. Not financial advice.

See more from StockTitan in Google Search and AI answers. Adds StockTitan as a preferred source · opens Google

Add on Google Not now

Dave Lupica Named Executive Chairman; Dave Roberts Appointed Division President

NEW YORK, Aug. 4, 2026 /PRNewswire/ -- Chubb (NYSE: CB) today announced key executive appointments within Westchester, the company's wholesale excess and surplus (E&S) lines business in North America. Dave Lupica, Vice President, Chubb Group and Division President, Westchester, has been named Executive Chairman. Dave Roberts, currently Chief Operating Officer, Westchester, has been appointed Vice President, Chubb Group and Division President, Westchester, succeeding Lupica. The appointments are effective immediately.

As Executive Chairman, Lupica will provide governance oversight and advise on strategy for Chubb's wholesale E&S business in North America. During his 26 years with Chubb, Lupica has played a pivotal role in the company's growth and evolution. From building Chubb's Financial Lines practice and launching the company's first Small Business division within Commercial Risk Services, to leading Westchester's digital transformation and growing Healthy Paws into one of the industry's leading pet insurers, his impact has been significant. Lupica's contributions to the E&S market were recognized in 2024 when he was inducted into the Insurance Business America Hall of Fame.

Roberts will have executive operating responsibility for Chubb's wholesale E&S lines business in North America and will oversee the delivery of Westchester's tailored specialty products for wholesale brokers. He 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," said 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, said of Roberts' appointment, "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 40 years of insurance industry experience to the Executive Chairman role. He joined Chubb (ACE) in 2000 as Executive Vice President of ACE USA's Professional Risk Division and later served as Division President of ACE Commercial Risk Services and Division President, ACE Westchester Professional Lines. He was appointed Chief Operating Officer and Distribution Management Officer of Westchester in 2016 and named Vice President, Chubb Group and Division President, Westchester, in 2024.  Before joining ACE, he held management positions at 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 served as Chief Operating Officer of Westchester since 2025, with operating responsibility for Chubb's wholesale E&S lines business in North America. As a nearly 20-year veteran of the insurance industry, he has spent more than a decade with Westchester, where he previously served as Executive Vice President, Head of Digital and Middle Market, and held senior leadership positions overseeing the division's Small Business products and business development, underwriting operations and profitability performance. He holds a Bachelor of Science degree in Management from Penn State University.

About Chubb
Chubb is a world leader in insurance. With operations in 54 countries and territories, Chubb provides commercial and personal property and casualty insurance, personal accident and supplemental health insurance, reinsurance and life insurance to a diverse group of clients. The company is defined by its extensive product and service offerings, broad distribution capabilities, exceptional financial strength and local operations globally. Parent company Chubb Limited is listed on the New York Stock Exchange (NYSE: CB) and is a component of the S&P 500 index. Chubb employs approximately 45,000 people worldwide. Additional information can be found at: www.chubb.com.

 

View original content to download multimedia:https://www.prnewswire.com/news-releases/westchester-a-chubb-company-announces-key-leadership-appointments-302842491.html

SOURCE Chubb

FAQ

What leadership changes did Chubb (NYSE: CB) announce at Westchester on August 4, 2026?

Chubb announced that Dave Lupica became Executive Chairman of Westchester and Dave Roberts was appointed Vice President, Chubb Group and Division President, Westchester. According to Chubb, these leadership appointments for the wholesale E&S business in North America are effective immediately.

Who is Dave Lupica and what is his new role at Westchester, Chubb’s wholesale E&S business?

Dave Lupica is now Executive Chairman of Westchester, Chubb’s wholesale E&S lines business in North America. According to Chubb, he will provide governance oversight and strategic advice, drawing on more than 40 years of insurance industry experience and 26 years with the company.

Who is Dave Roberts and what responsibilities does he have as Westchester Division President at Chubb (CB)?

Dave Roberts has been appointed Vice President, Chubb Group and Division President, Westchester. According to Chubb, he holds executive operating responsibility for the wholesale E&S lines business in North America and oversees delivery of Westchester’s specialty products for wholesale brokers, reporting to Scott Meyer.

How much industry experience do Dave Lupica and Dave Roberts bring to their new Chubb Westchester roles?

Dave Lupica brings more than 40 years of insurance industry experience, including 26 years with Chubb. According to Chubb, Dave Roberts is a nearly 20-year industry veteran, with over a decade at Westchester in senior roles across digital, middle market and small business operations.

When do the new Westchester leadership appointments for Dave Lupica and Dave Roberts at Chubb (NYSE: CB) take effect?

The leadership appointments of Dave Lupica as Executive Chairman and Dave Roberts as Division President at Westchester are effective immediately. According to Chubb, these changes apply to the company’s wholesale excess and surplus lines business in North America from the announcement date, August 4, 2026.

To whom will Westchester Division President Dave Roberts report within Chubb’s North America Insurance organization?

Dave Roberts will report to Scott Meyer, Senior Vice President, Chubb Group and Chief Operating Officer, North America Insurance. According to Chubb, Roberts will manage executive operating responsibilities for the wholesale E&S lines business and product delivery to wholesale brokers across North America.