[1] Cowpland worked for Bell Northern Research (later part of Nortel Networks), then MicroSystems International.
In 1973, Cowpland and Terry Matthews founded Mitel Corporation, a company that developed and sold electronic PBX systems.
In 1996, he offered a challenge to Microsoft with a move into productivity software, acquiring WordPerfect from Novell for $158 million.
He was investigated by the Ontario Securities Commission (OSC) in 1999–2000 regarding allegations that he had used insider information to sell $20 million in Corel shares at $8/share shortly before the company posted disappointing results.
[5] After an unsuccessful attempt to buy Borland with a view to creating a critical mass for Linux, Cowpland left Corel in August 2000, and moved on to buy control of ZIM corporation, a database and mobile content company which is listed on the NASDAQ bulletin board (ZIMCF).