A company director died after being shot in the mouth at point blank range with a silenced pistol by armed robbers, a court has heard.
Akhtar Javeed died with his hands bound "in a pool of his own blood" on a pavement outside his delivery firm's Birmingham warehouse in February.
He was also shot in the throat, leg and foot after refusing to open the safe, Birmingham Crown Court was told.
Suraj Mistry, 26, and Lemar Wali, 18, deny murder.
The pair also deny conspiring to rob and possessing firearms with intent to cause fear of violence.
Prosecutor James Curtis QC said Mr Javeed - a grandfather known affectionately by staff as Big Brother - was shot four times during the raid on the Direct Source 3 site.
The man who fired the gun was 25-year-old Tahir Zarif, of Osmaston Park Road, Derby, who fled to Pakistan and is still at large, he said.
Mr Mistry, of Laundon Way, Leicester, is said to be the other gunman and is alleged to have driven Mr Zarif to Heathrow airport after the shooting.
Mr Wali, of Osmaston Park Road, Derby, is accused of driving the getaway vehicle from the scene.
Jurors were told they would see CCTV footage of two masked gunmen "[bursting] through the door, guns already in their hands", before taking staff prisoner and binding their hands.
Mr Curtis said Mr Javeed, a father-of-four from east London, was "terribly brave" during the robbery and tried to fight back.
He was ordered into a corridor "no doubt to get him to the safe and open it at gunpoint", but he refused. As he tried to escape, he was shot by Mr Zarif, the prosecutor said.
"He was able to burst outside, mortally wounded, where he collapsed on the pavement and died from the shock and the blood loss."
Mr Curtis said the men had help from an insider, Dutch national Sander van Aalten, 50, who pleaded guilty to conspiracy to rob at an earlier hearing. He had also carried out a reconnaissance of the premises.
Another man, Asif Aurangzaib, 25, also from Derby, denies a charge of conspiracy to rob.
The trial is expected to last five weeks.