For Robert O’Leary, the new CEO of Philadelphia Insurance Company, the days when he peeled himself out of the driver’s seat of an unairconditioned car to sell casualty insurance policies around Boston are a distant memory.

“I had one suit that seemed to me to be in a standard state of disarray,” says the former road warrior, fondly recalling his humble beginnings and a 36-year journey to the much more comfortable driver’s seat of a profitable specialty insurance company in Bala Cynwyd, Pa.

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