He was a grandchild of Jacob Cornelisz van Oostsanen, who probably taught him to paint, and a cousin of Dirck Jacobsz.
This was printed in 12 blocks of wood, and was recopied and reprinted as an accurate map until well into the 17th century.
He also made several portraits of heads of state, and allegorical prints.
Only two of his paintings survive that have been attributed to him, a very early example of the militia group portrait or schutterstuk, the 1533 Banquet of Members of Amsterdam's Crossbow Civic Guard (Braspenningsmaaltijd) with a stiff and unsubtle depiction, and a portrait of Reinoud III van Brederode.
His popular bird's eye view of Amsterdam was copied in 1652 by Jan Micker and completed with cloud shadows over the land.