Phillip Posnett, of Haughton Hall, Hall Lane, Haughton, Tarporley, pleaded guilty to breaching Section 2 of the Health and Safety at Work Act 1974.
He was fined £16,000 with over £3,330 in costs.
Liverpool Magistrates’ Court heard how Mr Posnett's employee, Ian Kirby, was tasked with replacing broken tiles on a roof on 13 November 2014.
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After completing the repair, Mr Kirby then stepped onto an adjacent fragile roof to remove debris.
He fell several feet through the skylight into a tractor scraper parked below.
His injuries included a broken collar bone, broken ribs and a chip to the spine as well as head injuries. As a result of his injuries, Mr Kirby was unable to return to work for six months.
A Health and Safety Investigation found there was no suitable and sufficient risk assessment of the job. Ian Kirby had not undergone specific training for working at height. He had been given no information or instruction on the potential risks in relation to roof work.
HSE inspector Jane Carroll said: "Falls through fragile roofs are a well documented hazard when undertaking roof work of any type. This case highlights how a failure to risk assess a job properly and identify the presence of a fragile roof can lead to serious personal injury for workers."
(LM)
