For one year, he studied at the London School of Economics (LSE) in the United Kingdom,[4][5] where he became president of the Afro-Caribbean Society, a multi-ethnic group.

Issa graduated in 1988 from Holy Cross, cum laude, as valedictorian with membership in Phi Beta Kappa, Alpha Sigma Nu, and Omicron Delta Epsilon.

He was subsequently promoted to Senior VP of Sales in 1996, and initiated a customer satisfaction program which led to increased bookings and sustained brand loyalty through repeat visits.

[citation needed] In 1999, when Issa became executive vice president, he instituted marketing programmes, including the establishment of a new website to take reservations online 24/7, which led to higher occupancy levels.

IN 2014, it is one of the leading retailers of automobile-related lubricants and accessories in Jamaica, and also sells basic household products such as toilet paper and soap.

In 2000, Issa participated in media discussions on the impact of the high murder rate on foreign direct investments (FDIs) and economic growth in Jamaica.

[19] Issa also commented on the state of the tourism industry, advocating for government support to the small hotel sector and seeking to stem a brewing controversy of variable head tax rates for different cruise ship ports.

[24][25] Issa represented the island's 13 Chambers of Commerce during negotiations with the government concerning the Cess on street lights, intervening to avoid a threatened protest march.

The school adopted the program,[29] and the Fund was officially launched by Jamaica's then Acting High Commissioner in London, Dale Anderson.