Proude seems to have been the first member of his family to have settled in Canterbury, although his own links with his native parish of Sellindge, several miles to the south of the city,
Proude’s public career was divided between his official duties in the shire, as tax collector, commissioner and coroner, and his commitments in Canterbury as a jurat and six times’ bailiff. In April 1385 the sheriff of Kent was ordered to elect a coroner in his place after he was reported to be dead, but this was a mistake, for he remained in office another six years until, in the spring of 1391, a new order to the sheriff demanded his replacement, this time on the ground that he was ‘insufficiently qualified’. He had become prominent in Canterbury by February 1386, when he joined with five other leading citizens in soliciting the Crown for a grant of £200 to be spent on urgently needed repairs to the city walls. The work had already begun when he was chosen bailiff at Michaelmas, with Henry Lincoln as his colleague; and because the two men ‘travailed diligently’ during their term, the King, in the belief that the task might be more quickly completed were they to remain bailiffs for a further year, issued an order for their re-election in September 1387. Nevertheless, the works, after being carried on for several years, eventually came to a standstill, despite the fact that the bailiffs had spent the grant of £200 and more than twice that sum in addition.
In July 1389 Proude joined a syndicate to purchase from the Crown certain properties in Hythe and its neighbourhood (near his home at Sellindge), which had been forfeited by Sir Robert Bealknap, c.j.c.p., in the Merciless Parliament of the previous year. Late in Richard II’s reign he and John Pirie applied for royal permission to grant three messuages in Canterbury to a chaplain at the parish church of St. Mary Bredman in return for certain religious services, but although the local jury could find no reason to reject their request, a licence was apparently never issued. In 1400, in fulfilment of the will of Henry atte Stone, Proude gave a quarter of barley grown at Herne to Harbledown hospital near Canterbury. He appeared as a surety at the Exchequer in May 1405, in connexion with a lease of alien priory estates in Kent.
It is likely that Proude was dead by November 1409, when his son, William, joined other citizens of Canterbury in acquiring a royal licence to make a grant in mortmain to the commonalty as an endowment for continuing renovation of the city walls; certainly, by October 1411 he was no longer in possession of his house near St. Margaret’s church. He was survived by his third wife, Christine.