As long as Bob O’Leary can remember, the insurance industry has often struggled to attract young people to its ranks.

Executive Summary

The retiring of baby boomers has left many insurance companies with vacancies they'd like to fill with millennials. But in order to attract young adults to an industry they view as "stodgy," insurers first need to understand that millennials have a very different way of looking at work and life.

The 59-year-old president and CEO of Philadelphia Insurance Cos. has been in the property/casualty insurance business since 1977 and with Philadelphia since he was 26. Throughout his career, he said, young adults haven’t always wanted to be associated with a business that has long had a stodgy reputation.

“I still remember going to cocktail parties when I was first married and my wife would be embarrassed when I told [folks] I was in the insurance business,” O’Leary recalled during a Carrier Management interview. “The old joke was if you couldn’t get a job, you could go into the insurance business.”

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