Ashley Highfield is Chairman of Oyster Yachts Limited (since May 2018), makers of luxury British sailing boats. He is also founder of Henley Partners limited, his vehicle for investing in and advising businesses across a range of sectors. He is an Associate Director of Deloitte LLP. Between 2011 and 2018 he was CEO of Johnston Press plc. He has also worked for Microsoft as UK MD and the BBC as main board director for New Media and Technology, where he was responsible for the development and launch of the iPlayer.
Throughout his career, Ashley has been involved in a number of investments. Whilst at Flextech plc/Telewest plc (now Virgin Media) he led the acquisition of WayAhead Group (now See Tickets) and became executive Chairman. He led the investment in MultiMap (subsequently successfully exited to Microsoft) and became a NED. He made a further three investments where he joined the board of each company.
Whilst at the BBC, Ashley led the acquisition of Douglas Adams' business H2G2 (The online HitchHikers Guide to the Galaxy) and incorporated it into BBC Online.
Following the successful launch of the BBC iPlayer, he was instrumental in the creation of Project Kangaroo, the three way video-on-demand joint venture between BBC, ITV, and C4, and was subsequently appointed CEO.
In 2016 he led the acquisition of the i newspaper for £24m (out of the Independent/Evening Standard Group) and within 2 years had doubled profits from £5.5m to over £12m.
Ashley is helping entrepreneur Richard Hadida (who created Evolution Gaming from start-up with a current market cap of over €2 billion) successfully turn around Oyster Yachts Limited, bought during early 2018.
Ashley is advising a well known Classic and Super Car business on their digital strategy.
He has also created a digital start-up, Project LocalEyes, an app which aims to help SMEs create and place adverts onto local publishers' websites. It was announced in March 2019 that Project LocalEyes had received Google funding as part of the Google Digital News Initiative (DNI).
He is an Associate Director of Deloitte LLP.
He has passive investments in a number of British tech start-ups including: Istesso Limited, Medaphor Group plc, Bloom and Wild Limited, Senseye, Brightpearl Ltd, SLAMcore Limited, Senseon and Peak Business Insight Limited.