In 1915 at the outbreak of World War I, he joined the 95th Battalion with the rank of Captain. He did his basic training at Wellington Barracks Halifax, where he had married quarters, so that his family moved with him. Fortunately when he went overseas, his family moved out of the barracks and into her parent's home in Halifax. On 8 December 1917, Wellington Barracks along with half of Halifax was destroyed when two ships, one of them full of explosives collided. The house they were living in was spared the worse.

Richmond who had been transferred overseas in 1916, served in the First Canadian Division of Engineers. He served in France as an Adjutant, until 1917 when he was promoted to Major in Command of the 9th Field Company.

On his return he joined the Eastern Trust Company as Assistant General Manager at Halifax. He was appointed general manager in 1924. In 1926, he moved his family to Montreal, where he became Secretary, and board member of W.C. Pitfield, an investment company.