Woolfe, who is currently director of programmes for Sky 1, 2 and 3, will be responsible for the commissioning, scheduling and strategy for Five's main channel.
He will report directly to Airey, and sit on the executive board alongside Jeff Ford, who is joining Five as managing director, digital channels and acquisitions, from Channel 4. Director of programmes for Five, Ben Gale, will be leaving the channel.
Airey said: 'Richard is the greatest showman working in British television today. He has a sixth sense for commissioning and producing popular programming that truly strikes a chord with viewers. He will bring a tremendous energy, creativity and chutzpah to the Five brand and I'm thrilled to be working with him again.'
Airey hired Woolfe from Living to run Sky 1 in 2006, when she was managing director of Sky Networks.
Woolfe said his aim was to put entertainment at the heart of the Five to 'complement and build upon the existing successful programme brands'.
During his time at Sky, Woolfe acquired celebrated US dramas Lost and Prison Break.
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