Johan (Jan) Wittebol arrived at the Cape in 1669 in the employ of the Dutch East Indian Company, with the rank of midshipman. In addition to clerical duties he was expected to do survey work. In March 1670 he was promoted to assistant and surveyor, and in April 1672 to junior merchant. He was the company's shopkeeper, but his work in this connection was so unsatisfactory that he was discharged and demoted to soldier in 1673. However, he was an educated man and also held the post of school-teacher. In 1678 he was co-opted as a member of the Council of Policy and in April 1680 became an ordinary (rather than co-opted) member of the council. In September 1674 he married Maria Ruyveen, with whom he had a son.
Wittebol was a competent surveyor and an architectural draughtsman of the highest quality. Among others he surveyed and mapped Hottentots Holland (1671), and was instructed to compile the first map of Stellenbosch in 1680, though no such map has survived. He also made two excellent pencil sketches of the Castle, which was being built at this time. These were titled 'T Casteel De Goede Hoop in het perspectief van de waterkant af te sien (The Castle of Good Hope in perspective as seen from the shoreline) and Platte grondt van't Casteel de Goede Hoop (Plan of the Castle of Good Hope). The drawings are in the State Archives in The Hague.