Over the past two decades, Business Insurance’s Women to Watch Awards have recognized hundreds of exceptional executives who have made a lasting impact on the insurance and risk management industry.

To celebrate the 20th anniversary of Business Insurance's Women to Watch awards, we named 10 Iconic Leaders from among our past winners — a group of executives who have gone on to achieve extraordinary success. We spoke with them to learn about the choices that shaped their careers, what it means to be a “leader of leaders,” the value of teamwork and even their favorite day of the week to connect.

A spike in thefts, including a brazen daytime heist of eight historic jewelry pieces from the Louvre in Paris, has highlighted the targeting of objects for their commodity value and should prompt museums to reassess their security measures.

Higher reconstruction costs faced by the commercial property/casualty insurance industry are being driven more by rising labor costs than by materials, according to recent data and industry sources.

As the workforce ages, the workers compensation industry faces a convergence of pressures that include rising claim severity and litigation pitting injury causation against preexisting conditions, with many disputes fueled by a familiar diagnostic flashpoint: magnetic resonance imaging.

Nursing professionals should carefully document patient care to avoid malpractice claims, which experts say are increasing in severity.

Companies are increasingly aware of the risks of compromised technology systems and data theft, but they also face potential cyber exposures that don’t entail a security breach. 

Small and mid-sized businesses are increasingly in the crosshairs of cybercriminals, with 61% of those surveyed reporting they experienced a cyberattack last year.

Police officers, firefighters and paramedics run toward danger while others flee.

With the 20th anniversary of the Women to Watch awards, I was reminded how some qualities of our winners remain consistent year after year, while others reflect current trends and shifts in the workforce.

As 2025 winds down, the first quarter of the 21st century also comes to an end, which, for many of us who remember the turn of the millennium, vanished with remarkable speed.