Born in 1869 in Bras d'Or, Nova Scotia, Ross went to work for the Bank of Nova Scotia emptying wastebaskets at the age of 14. The family farm had failed and Ross left school in order to earn money . He rose through the ranks, becoming manager of branches in Stellarton and New Glasgow before becoming manager of the Charlottetown branch at the age of 24.[1]
In 1901, he joined the Ministry of Finance in Ottawa before becoming general manager of the Metropolitan Bank of Toronto and moving to Toronto with his wife and children.[1] In his new city, Ross helped find the funds to found Branksome Hall, a new private school for girls, operated by his cousin. In 1914, the Metropolitan Bank was acquired by the Bank of Nova Scotia, where Ross would ultimately become vice-president and sit on the board of directors.
Ross's first wife, Susan Archibald McGregor, died in 1909. Her father would become Lieutenant Governor of Nova Scotia. They had three children: Donald, Isabel and Susan. He later married Isabel MacKay and they had two children: Jean and John.[1]