Robert Rogers, 61, was working for Richard Parker, trading as Ovenden Engineering, which had been contracted by Allied Domecq Spirits and Wine Ltd to fix a leak in the roof and clean the gutters of their bonded warehouse in Dover, Kent.
Canterbury Crown Court was told that Rogers was on the roof with his brother, Trevor, also an employee of Richard Parker, when he fell through one of the 80 skylights and hit the concrete floor below.
He suffered multiple injuries and died later in hospital.
Rogers, known as Bob, of Folkestone, left his wife Jennifer, two sons and nine grandchildren.
The court heard there was no safety equipment in place for anyone working on the roof – despite Parker’s employees working on the warehouse roof as often as every month.
There were no crawling boards, scaffolding boards, harnesses or nets to protect workers from the risks.
As the owner of the warehouse, Allied Domecq had responsibility for the site and should have ensured contractors planned their work and carried it out safely and that proper control measures were in place.
Richard Parker, t/a Ovenden Engineering of Folkestone, Kent was fined £26,667 and ordered to pay £4,000 in costs after admitting safety breaches.
Allied Domecq Spirits and Wine Ltd, t/a CG Hibbert, of Chancellors Road, West London, was fined £266,677 with costs of £10,752.
Both defendants had entered guilty pleas at a hearing before Canterbury Magistrates in April.
After the sentencing hearing, HSE Inspector Guy Widdowson said: “This is a tragic case in which a devoted husband, father and grandfather has lost his life whilst at work.
“It is sickening that such incidents happen despite the widespread industry knowledge of the risks of working at height and of working on fragile roofs with equally fragile skylights.
“Mr Rogers’ death was entirely preventable. Mr Parker should have provided his workers with suitable equipment to work on the roof. He failed to do so.
“Allied Domecq do not contract out their health and safety responsibilities just by contracting out a particular job.
“It was their duty to ensure there was a safe system of work before the job started and that their contractors followed agreed safe procedures. They too failed to do so.”
In a statement to the court, Mr Rogers’ wife of nearly 40 years, Jennifer, said: “The shock and suddenness of Bob’s death significantly affected me.
“I was in a daze for a long time, and still find I’m in a daze now sometimes.
“His death was just after my birthday and near Christmas and I found it very difficult to face Christmas without him. I feel lost without him and do struggle.
“I miss him terribly. I miss talking things over with him.
“Bob used to help our sons a lot with DIY and we all miss him not being here to help, he was very knowledgeable.
“My life is empty now without my lifelong companion by my side. He was my soulmate- we did everything together.”