In 1896 Pitman was elected to the Henley Royal Regatta management committee, filling the vacancy caused by the death of J. H. D. Goldie.
The Cambridge crew were upset by the mistake and certainly did not row at their normal standard, but the effect of the error was disastrous for Oxford who never recovered.
In 1919, Pitman became Chairman of the Henley Royal Regatta management committee in place of the recently elected W. A. L. Fletcher, who had died from influenza.
He held the role until 1944 and unlike his predecessors, had no desire to get involved directly in the running of the regatta, describing his position as "Chairman of the board with the particular function of finding the finance if Tom Steward over-reached himself".
They had three daughters; Anna Dorothy (1892–1972), who married Sir Ronald Forbes Adam, 2nd Baronet, and Isabel Mary (1891–?