When you’re a smaller athlete competing with giants, sheer determination and sharp reflexes are tools you might use to glide past opponents—and a winning formula in business isn’t too different, according to one insurance leader.

“We punch way over our weight,” Lou Iglesias, the chief executive officer of Global Insurance for Allied World, told Carrier Management several times during a recent hour-long interview at the company’s New York offices in late September. In the world of insurance, Iglesias describes Allied World as a midsize insurer operating in a large-account world against insurers with 20-times as many employees....

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