
After two decades moving from underwriting spreadsheets to startup experiments and nationwide distribution, Steve Chauby has arrived at a deceptively simple idea: give educators choice, remove friction and show up where their lives actually happen.

She began as an investor-relations analyst and stayed for the long argument. Two decades later, Suzanne Shepherd's remit spans marketing and sustainability - proof that the people who explain a business can end up helping shape it.

From underwriting desk to chief marketing officer, Michael Sheeley's four-decade UFG career is a study in institutional memory, earned range and the quiet power of showing up.

After three decades studying catastrophe risk from boardrooms in New York and Bermuda, Steve Weinstein chose Florida for his founder’s bet. Mangrove’s strategy is equal parts underwriting discipline, global reinsurance and a stubborn belief that difficult markets can still reward patient builders.

From a family brokerage in Cloverdale to the C-suite and a national board seat, Christine Young has built a career around a deceptively simple idea: insurance works better when people stay close to one another.

At HUB International, Sarah Thompson translates hidden exposures into practical action. Her other proving ground is a three-day trail race, where organizing 200-plus volunteers turns preparation into something you can see.

At The Baldwin Group, a veteran insurance marketer faced a rare assignment: turn a collection of nearly 40 regional identities into one national promise without sanding away the expertise underneath.

After building products for small-business owners, the former Capital One and American Express executive has taken on a broader experiment at Hiscox: joining customer insight, product, distribution and growth in one job.

Her career began with a deferred law-school seat. It now runs through the customer office, where an old insurer is learning to make trust visible, usable and current.

After a career spent translating pressure into clarity - from Washington to AOL, EY and now Chubb - Amy Call Well is betting that the communicator's real job is to find the signal people can trust.
Mario Vitale is CEO of Resilience Cyber Insurance Solutions and President of Resilience, a cyber risk company that fuses cybersecurity, insurance and incident recovery into a single offering. A native New Yorker with more than 40 years in insurance, he previously ran Willis North America, Zurich's Global Corporate business and Aspen's global insurance operations before coming out of semi-retirement to help build Resilience alongside military-veteran founders Raj Shah and Vishaal Hariprasad.
Alison Richards is the CEO of Surest, a UnitedHealthcare company (formerly Bind) that builds a health plan with no deductibles and upfront prices people can see before they book care. A UnitedHealthcare veteran since 2012, she has turned the company's most contrarian benefits idea - let members shop for care the way they shop for everything else - into its fastest-growing employer plan.