Henry started his administrative career as a bailiff for the Honour of Berkhamsted in 1221, succeeding Hugh as Under-Sheriff of Berkshire from 1228 to 1229.
From 1229 to 1232 he served as Under-Sheriff for Hampshire and as High Sheriff of Gloucestershire from 1232 to 1234, a time when the county was the main base for the Marcher Wars of 1233–34.
In 1241 he went on a mission to Ireland, and on his return served for two terms as a justice coram Rege (in the presence of the King) until 1242.
After Henry III left for his trip to Gascony in 1242 he was appointed High Sheriff of Yorkshire, a position he held until 1248 (although it was administered by his deputies from 1245 onwards).
Henry came back into royal favour in 1253, shortly before another of the king's journeys to Gascony, and was made Chief Justice of the Common Pleas yet again in 1256, serving until 1258.