In 1786 his Salisbury-born father, with his partner Samuel Watkins, had opened a tobacco shop in Bristol, which grew into a successful business.
[2] Henry and his elder brother William Day Wills in 1815 joined their father's firm, and became co-owners of the company in 1826 when he died.
In 1859 Henry made his son Edward Payson Wills a partner in the firm, who succeeded to his father's interests in the company.
Wills II entered local politics in 1845 as a City Councillor for the St. Pauls district of Bristol and he continued to serve on the town council for several years until hearing problems forced him to retire from public duties.
Wills II married twice: He died on 23 November 1871 in Bristol, and is buried in Arnos Vale Cemetery.