Gheisar began coaching with youth soccer club North York Hearts-Azzurri SC in 2005.[3] Afterwards, he joined Vaughan Azzurri as a youth soccer coach where he remained in various roles for 16 years until 2022.[4]
He also served as an assistant coach with Portugal FC/SC Toronto in the Canadian Soccer League under Carmine Isacco.[1] In 2011, he was nominated for the Coach of the Year award while managing SC Toronto's reserve team in the CSL's second division.[5] In 2012, he was named head coach of the first team, after Iascco moved to the role of Technical Director.[6]
At the university level, he served as an assistant coach with the Ryerson Rams and York Lions.[2]
In December 2018, he was announced as the head coach of the Seneca College's men's soccer team at the college level.[7] With Seneca, Gheisar was named OCAA coach of the year in 2019.[8]
He also served as coached Vaughan Azzurri in League1 Ontario, under Carmine Isacco (who he also worked with at SC Toronto and with the York Lions).[9][10] In 2019, he was named head coach of the League1 Ontario side, taking over from Isacco.[11] In 2019, Vaughan participated in the 2019 Canadian Championship, defeating professional club HFX Wanderers FC 1-0 on the road in the second leg, but were eliminated on away goals in the two-legged tie.[12] In 2021, he was named East Division Coach of the Year,[13] and the following season was named the overall league Coach of the Year.[14]
On November 30, 2022, he was named head coach of HFX Wanderers FC of the Canadian Premier League.[15] At the time of his hiring, Wanderers president Derek Martin emphasized Gheiser's history of developing strong attacking teams and his recruitment ability as prime reasons for his hiring.[16][17] He won his first professional match on June 10 in a 2-0 victory over Valour FC and was named the CPL Manager of the Month for June.[18] After his first season, he extended his contract with the club through 2025.[19] In November 2024, he was invited to join the Canada men's team to assist with their training camp as part of Canada's Community Coaching program.[20] After the 2025 season, he parted ways with the club, upon the conclusion of his contract.[21][22]
In January 2026, he joined Scrosoppi FC as their Director of Football Operations and head coach of the men’s first team in League1 Ontario.[23][24]
