Allan Thompson, of Woodburn Crescent, Bonnybridge, Stirlingshire, was found guilty of gross negligence manslaughter, while both he and his company Building and Dismantling Contractors were found guilty of offences under the Health and Safety at Work Act and for breaching regulations of the Work at Height Regulations.
Mr Thompson was jailed for six years and fined £400,000 with £55,000 in costs.
His company had been subcontracted by C. Smith and Sons to level the Harvey's and Carpetright buildings in Heaton Norris, Stockport in 2014.
Michael Smith of Lightowlers Lane, Rochdale, and his company C. Smith and Sons, were found guilty of offences under the Health and Safety at Work Act, as well as breaches in both CDM Regulations and Work at Height Regulations.
He was jailed for eight months and fined £90,000 with £45,000 in costs.
Manchester Crown Court heard how C. Smith and Sons had won the contract to demolish the buildings and it was originally planned that plant machinery would be used to remotely bring down the structure.
However, Mr Smith decided the building should instead be dismantled piece by piece, meaning workers would be required to remove materials at height prior to the structure being unbolted.
Subsequently, four men employed by Building and Dismantling Contractors travelled to Stockport to carry out the work on 15 January 2014.
The roof of the building was made up of steel corrugated sheets with interspersed plastic skylights, which had deteriorated over time and had subsequently been covered with corrugated steel sheets in a bid to repair the damage.
On 20 January 2014 one of the men, 42-year-old Scott Harrower, accidentally stepped through a skylight and nearly fell 30 feet to the floor below.
On that occasion he managed to prevent himself from falling, but the near miss did not prevent the men from returning to carry out their work the next day.
Just after 9am on Tuesday, 21 January 2014, a 47-year-old member of the group fell through a skylight to the floor below and fractured his spine, pelvis, right leg, heel and wrist.
Despite the incident, the men were ordered to return to the work hours later and at 4pm Mr Harrower fell through a skylight.
He suffered catastrophic head injuries and died as a result.
Detective Chief Inspector Richard Eales said: "First and foremost, our condolences go to the families of Scott and his colleague, who were the victims of both companies' criminal negligence and who died in tragically preventable circumstances.
"It is clear from the evidence that both Smith and Thomson saw an opportunity to make a quick profit without any thought for the workers they sent on to the roof, and as a direct result of that greed Scott died and another man suffered life-changing injuries.
"Smith and Thomson's remorse did not then stretch to admitting their guilt, as both tried to hide behind their companies and refused to plead guilty to the charges levelled against them personally.
"Thankfully, the jury saw through their attempts and both now can face justice for the decisions that they made, decisions that have robbed one family of a loving partner, father, and son, and another of a man's ability to live a life untainted by severe physical injury."
(LM)
