With the support of relatives including his cousin; politician and planter Howell Donald Shillingford, he expanded into agriculture, acquiring estates that produced limes, oranges, bananas, sugarcane, and other crops.
This expansion directly challenged the monopoly held by the British-owned L. Rose & Co, allowing local lime growers to secure better prices for their produce.
He was a financial backer of the 1932 Dominica Conference, which was attended by regional political figures, including Arthur Cipriani of Trinidad and Theophilus Marryshow of Grenada.
Shillingford was noted by the British colonial administration for his criticism of the treatment of West Indian soldiers who served in World War I.
His funeral garnered a large number of people from all walks of life, the procession began by leaving his home at New Street, In Roseau, where all the shops closed and the banks flew their flags at half-mast to pay their respects.