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Tom Hickey has a diverse and extensive work experience. Tom started their career at Imprint, Inc. in 1983, where they worked as the Director of Corporate Communications and Associate Publisher for almost seven years. In 1990, they joined Capital Cities/ABC, Inc. as the Director of Marketing, where they successfully created and executed a corporate identity and culture for the newly formed New England Newspaper Group. Tom also founded SuperNET, a networking platform for suburban newsweeklies in New England.

In 1995, Tom Hickey started Hometown Marketing, a company they formed with Creative Partner, Joy Taylor. As the Publisher, Marketing Director, and Partner, they specialized in target marketing media buys for various clients, such as Cherry & Webb and Foxwoods Resort Casino. Tom also strategically planned, organized, and implemented a network of Playbill Publishing in Connecticut, streamlining the publishing process for the Arts Organizations and sharing profits 50/50.

In 2000, Tom Hickey became the Publisher of Living In West Hartford Magazine, Living In The Valley Magazine, and Living On The Shoreline Magazine. These were the first lifestyle magazines in the region targeting homes with a household income of over $100,000. Tom also started Help & Hope Magazine for Catholic Charities of the Archdiocese of Hartford.

Starting in 2011, Tom Hickey held multiple roles within WHMEDIA and West Hartford Media Group. As the President, Publisher, and Marketing Director, they oversaw the operations of WHMEDIA and its various publications, including West Hartford Magazine, We-Ha.com, Dazzle, Palette, Help & Hope, Stanger & Arnold, and Monarch Jewelers. Tom also started Farmington and Avon Magazine. Additionally, they served as the Marketing Director for West Hartford Media Group.

Most recently, in 2020, Tom Hickey became President of 2020 Media/Ledger Publications.

Tom Hickey began their education at St. Brigid School, where they attended from 1966 to 1974. Tom then moved on to Northwest Catholic High School, where they continued their studies from 1974 to 1978. After completing high school, Tom attended Central Connecticut State University, where they pursued a Bachelor of Arts (B.A.) degree in Corporate Communications & Marketing from 1978 to 1982.