Sherry started his working life as a night cashier and auditor at the Wrest Point Hotel and Casino in Hobart. While working at Wrest Point, Sherry joined the Federated Liquor and Allied Industries Employees' Union and became State Secretary of the then FLAIEU between 1979 and 1990. In 1992, the FLAIEU amalgamated with another union to form the present day Liquor Hospitality and Miscellaneous Union (LHMU).
While State Secretary, Sherry also helped establish the HostPlus Superannuation Fund, an industry superannuation fund then only for hospitality industry workers, but now a full public offer fund with over $7 billion under management. Sherry held the position of trustee of HostPlus from 1987–1990 and was also a trustee, manager, and company secretary of ClubPlus Superannuation fund. Sherry held positions on the State Executive of the Tasmanian Trades and Labor Council from 1988–1990 and was President from 1988–1990.
During his time as State Secretary, Sherry held a number of positions including Board Member at the College of Hospitality, Board Member of the Hospitality Group Training and Board Member of Employment and Skills Formation Council.
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