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Thomas J. Phelan


phelan-thomasAs CEO of the Chesapeake Employers’ Insurance Company, Thomas J. Phelan is focused on the day-to-day oversight of global strategy and direction as well as pursing innovative opportunities to expand their footprint.

Phelan first joined the Towson-based company in 1990 and took on various leadership roles, including serving as the chief financial officer before being named to his current position in 2007.

Away from the office, Phelan gives his time to several nonprofits, including being board chair for the nonprofit Kids’ Chance of Maryland Inc. and co-chair of the Franciscan Center.

What’s the most important lesson you’ve learned in your career?

During your career, and in working with others, try not to overreact to good or bad news. The best leaders I have worked with are very calm in both good and bad situations. Things are never as good as they look when they are going well and never as desperate as they appear when they are going poorly.

Who have been the biggest mentors in your career?

I believe my leadership style is a composite of many individuals. I am a strong believer that in any situation you can learn from your leader. When I worked for a poor leader I tried not to use their approach in dealing with others. When I worked for a strong leader I tried to emulate their behavior with others. The best leaders, in my opinion, try to make things better for others.

This profile is part of The Daily Record's Power 100 list for 2021. Information used in this profile was sourced from the honoree. See the full list at or in our digital edition.