Ross started his career as a planning engineer in the Township of Toronto (now the City of Mississauga).  Subsequently he formed Municipal Planning Consultants and then became president of the Triton Group.

In 1970, Ross became president of J. Ross Raymond & Associates Limited operating just outside of Gravenhurst.  Ross loved Muskoka and northern Ontario, and became actively involved in projects outside of planning—restoration and operation of the Severn River Inn in Severn Bridge and restoration of the RMS Segwun steamship.  Ross was the first president of the Muskoka Steamship & Historical Society and the first president and honorary director of the Muskoka Lakes Navigation and Hotel Company Limited, the company that operates this historic ship.

In 1991, Ross formed a new firm with Margaret Walton and Rick Hunter known as Raymond, Walton, Hunter.  That same year he was appointed as one of three Land Use Mediators by the Ontario Municipal Board, a role he later acknowledged to be the highlight of his career.

As a planner, Ross enjoyed working for a variety of municipalities across Ontario and often his were their first planning documents.  His extensive experience included specialty fields such as agriculture in southern Ontario, resort development in Muskoka, Haliburton, Parry Sound and Kawartha Lakes, and heritage planning in Niagara-on-the-Lake. 
Ross received the OPPI Member Service Award in 1995 for managing and moderating an ongoing professional development program for young planners about appearing before the OMB.  In 1998, Ross was inducted as a Fellow into the Canadian Institute of Planners.

J. Ross Raymond passed away in January 2012 after a distinguished career of over 40 years as a professional planner and civil engineer.  Ross will be fondly remembered as a mentor and professional planner who fiercely supported the institute and promoted the highest code of conduct for practicing planners.