Initially on a two-year contract, Winn – along with former public affairs chief Phil Burgess – was brought in by Sol Trujillo and was known as one of the three amigos being one of the trio of top American executives at Telstra.

A critic of the Federal Government's internet filtering programme, Winn headed Telstra's networks and operations, and has been a key driver of the transformation of the company's IT systems, networks, product development and procurement processes. He was integral to the building of Telstra's nationwide Next G mobile network, as well as the company's Next IP network.

Winn also oversaw delivery of field workforce productivity improvements focused on reducing costs while demonstrably improving the customer experience.