Sail started his career playing for Wanderers SC, a special club set up to develop players for the New Zealand national under-20 football team. In 2013, he joined Auckland City for one season. In 2014, he joined the Wellington Phoenix Reserves Team. On 3 March 2017, Sail signed his first senior contract, penning a two-year deal with Wellington Phoenix. On 25 March 2018, Sail made his A-League debut against Brisbane Roar in a 2–2 draw. On 3 March 2023, Sail confirmed that he would be leaving Wellington Phoenix at the end of the 2022-23 A-League season. He has now signed for Perth Glory on a three year contract.