Michael Hess was indentured into the Ironworkers Apprenticeship Training Program in 2000 at the age of 21 and served a three-year apprenticeship in Local 7 Boston. During his time in the field as an ironworker he worked in various facets of the trade, reinforcing, structural, miscellaneous metals and ornamental. Throughout his time in the field, he worked as a steward on various projects and worked as a foreman for several different signatories.

In 2012 he was elected to the executive board for three years, following that term he was elected President of the local in 2015. During his time as President, he became appointed to the Business Agent Boston/West position in 2016. In March of 2020 he was appointed to the role of Business Manager. Throughout this time, he held several positions including Trustee to the Boston Building Trades Council, Vice President to the Massachusetts AFL-CIO, Massachusetts Building Trades Council Executive Board Member and Board Member to the Massachusetts Coalition for Occupational Safety and Health.