Working with co-conspirator Scott Granville — with whom he founded production company Chasing Time in 2008 — Ben Woollen has directed feature film Pictures of You and collaborated on many short films, including award-winning comedy Serve and Protect and 42 minute romance They No Longer Sleep Alone. In 2017 the focus of the company shifted to making productions specifically for teachers and students of the English language. Outside of his work with Granville, Woollen works as a cinematographer under the banner of the Newtown Video Company. In 2015 he shot road movie Penny Black and short film Lapwing.
[Ben Woollen] said New Zealand has a lot of benefits and drawbacks to independent filmmaking, because it has more creative people in a smaller area but fewer platforms. Writer Chelsea Armitage, in a Waikato Times article on short film Serve and Protect, 11 August 2014