In 1971, Smallwood undertook a job at a London booking agency, Gemini. Soon moved to rival agency Management Agency And Music, Ltd. (MAM), working as a booking agent, after 18 months with them, he began managing English rock act Steve Harley & Cockney Rebel. In 1974 Harley started Trigram, his management agency, and Smallwood undertook the management of punk rock act Gloria Mundi.
In 1979, Smallwood contacted Iron Maiden's Steve Harris, and arranged two pub gigs for the group in London's west end. He was not the bands full time manager until arrangement of band's signing to EMI Records Ltd. and publishers Zomba Music Publishers Ltd. at the end of the year.
In 1976 alongside long term business associate Andy Taylor (16), Smallwood Taylor Enterprises Ltd., is established to provide creative management to music artists. In 1981 Sanctuary Music Ltd. is the first company to adopt the "Sanctuary" name (taken from an Iron Maiden track)
The holding company Smallwood Taylor Group Ltd. is established in 1985, subsidiaries at this time included: Sanctuary Music Ltd., Sanctuary Music (Overseas) Ltd., Ross Halfin Ltd., Fair Warning (8) Ltd., Sanctuary Productions, Inc., Sanctuary Music, Inc.. In 1988 Smallwood Taylor Group Plc is renamed The Sanctuary Group Plc (not to be confused with Sanctuary Records Group Ltd., which was a subsidiary of that holding company formed in 2000, following the acquisition of Castle Music Ltd.)
In November 2006, he resigned from The Sanctuary Group PLC (which is now known as Universal SRG Group Ltd. and forms part of the Universal Music Group) and formed Phantom Music Management Ltd. with Andy Taylor.
Current directorships (as of 2018)
- Sanctuary Management Productions Ltd.
- Helloween Ltd.
- Trooper Enterprises Ltd
- Focus Business Management
- Raw Power Management Ltd.
- Phantom Music Management
- Iron Maiden Overseas Ltd.
- Iron Maiden Publishing Overseas Ltd.
- Iron Maiden Holdings Ltd.
- Total Productions Ltd.
- Iron Maiden Ltd.
- Maiden Hell Limited
- Search And Destroy Records Ltd (2008)
- Twenty-First Artists Ltd. (2006)
- Sanctuary Records Group Ltd. (2006)
- Sanctuary Enterprises Ltd. (2006)
- Sanctuary Records Ltd. (1996)
- 1 Writing & Arrangement
- 5 Production
- 2 Technical
- 21 Visual
- 6 Acting, Literary & Spoken
- 106 Management