After a number of years working as an independent real estate contractor for different real estate companies in the Cayman Islands, in 2002 Sheena Conolly founded Sheena Conolly Real Estate and commenced a new era of white glove property service in the Cayman Islands. In recognition to the level of quality service and customer satisfaction in 2005 Sotheby’s International Realty approached Sheena Conolly to take on the master franchise for Sotheby’s International Realty in the Cayman Islands. Appreciating that the brand not only offered global reach but also a loyal and illustrious clientele accustomed to buying multiple luxury homes around the world Sheena Conolly seized the opportunity and on 15th December 2005 open the real estate gallery doors as Sheena Conolly Sotheby's International Realty re-branding shortly afterwards as Cayman Islands Sotheby's International Realty.