Increasing the number of people cycling to work brings a number of benefits: it can lead to reductions in air pollution and traffic jams, and increases people’s physical activity levels. We investigated the extent to which work-related factors influence (1) whether an individual decides to cycle to work, and (2) whether an individual cycles to work every day. It is anticipated that the office culture and colleagues’ and employers’ attitudes would significantly influence both decisions. These factors are expected to impact the provision of cycling facilities and financial compensation schemes in the workplace. We conducted an Internet survey in 4 Dutch municipalities, gathering data from over 4,000 respondents. The results suggest that the following factors increase the likelihood of being a commuter cyclist: having a positive attitude towards cycling; colleagues’ expectations that an individual will cycle to work; the presence of bicycle storage inside; having access to clothes changing facilities; and needing a bicycle during office hours. The presence of facilities for other transport modes, an increase in the commute distance, and the need to transport goods, in turn, reduces the chance that an individual will cycle. Cycling frequency is negatively affected, meanwhile, by an increase in commute distance, a free public transport pass or car parking provided by the employer. These results indicate that an individual’s working situation affects the commuting cycling behaviour. The findings also indicate that (partly) different variables influence an individual’s decision to cycle to work, and their decision to cycle every day.