Shillingford became a freeman of Exeter on 14 November 1418 and was active in civic affairs. He attended the 1417 shire elections at Exeter Castle and established himself as a
merchant. In 1421, he served as the mainpernor for
John Shapleigh II and his kinsman
Roger Shillingford, who were elected to Parliament, though records indicate that he was the one reimbursed for attending the Commons. On 1 December 1421, he was formally appointed as a constable of the local Staple by the Crown. Recognized for his administrative abilities, Shillingford was appointed a
feoffee for the foundation of
almshouses in Exeter and served as an executor of the will of William Wynard, the city recorder, alongside Chief Justice
John Fortescue. He was also frequently sent on business to London. Shillingford served as
Mayor of Exeter multiple times, including in 1444, when he initially resisted the appointment but was compelled to accept the role by a writ under the privy seal, facing a fine of £1,000 if he refused. According to the historian
John Hooker, he ultimately performed his duties well. Shillingford’s tenure as mayor coincided with a significant legal dispute between Exeter’s civic authorities and the cathedral leadership, led by Bishop
Edmund Lacy and the dean and chapter. His letters from this period provide insight into his leadership, negotiation skills, and personality. The bishop accused him of causing considerable disruption to both the church and the city. Shillingford traveled to London in 1447–48 to argue Exeter’s case before Chancellor
John Stafford and Chief Justice
John Fortescue. The legal battle proved costly, and Shillingford often referenced his financial difficulties in letters, writing that he was "right merry and fare[d] right well, ever thanking God and [his] own purse," and noting that "money is like to be scarce with me, considering the business and cost that I have had." Despite the expenses, he reportedly made a favorable impression on Stafford and later sought financial assistance from Archbishop
John Kemp for the reconstruction of Exe Bridge. == Family ==