Teesside Crown Court heard how, on 21 July 2016, the injured person had been in the process of installing a roof on the new restaurant in Coulby Newham.
While moving materials on the roof, he stepped backwards onto an adjacent fragile mesh roof that was not loadbearing, falling approximately three metres and suffering multiple fractures of his lower left back.
An HSE investigation found that in failing to prevent access to the fragile roof area, the roofing contractor, Metcalfe Roofing & Building Services Limited, had failed to plan and carry out the work at height in a safe manner.
The investigation also found the principal contractor PDR Construction had failed to plan, manage or monitor an aspect of the construction phase without risk to safety.
PDR Construction Limited of Hessle pleaded guilty to breaching CDM regulations and was fined £225,000 with £8,000 costs.
Metcalfe Roofing & Building Services Limited of Hartlepool also pleaded guilty to safety breaches and was fined £2,000.
After the hearing, HSE inspector John Heslop said: “This incident highlights the importance of thorough risk assessment, appropriate planning and adhering to a safe system of work that is regularly monitored and managed by those in control of that work.”