Ian Perry, who worked in primary schools such as Mossbank and Olnafirth, was involved in an accident near Mansfield on Sunday.
The 48 year old, also a bassist and vocalist for local band The Bluemelts, left Shetland at the end of last year to take up a post at Sherwood Junior High School in Mansfield.
He began work in Shetland Islands Council's education service in 2005 as manager of the behaviour support base in Lerwick and the community schools team in Brae.
One year later, Perry became head teacher of the Mossbank and Olnafirth primaries.
He left the isles in 2008 but returned a couple of years later to work as head teacher at Happyhansel and Sandness.
Before moving to Shetland, he previously worked in nursery, primary and secondary schools in North Yorkshire and Staffordshire.
Perry played bass guitar in local seven-piece band The Bluemelts, whose debut album 'Leave it Late' was released last year.
The group, recognisable by their brass sound, were a regular fixture on local radio station SIBC.
The Bluemelts' guitarist and vocalist Iain Malcolmson described Perry, who lived in Nesting, as an "excellent musician" who was first and foremost a good friend.
"Ian was a Yorkshire man, so he was gruff on the outside, but he was a kitten on the inside," he said.
"He was a talented musician and arranger - he did all the brass arrangements for the band.
"It was a complete shock to everyone. All the band members are devastated."
Perry also played upright bass for jazz collective Full Swing, and he was secretary of the Shetland Community Orchestra.
The 48 year old was a former member of the Shetland Rugby Club, and he was described as a "brute on the pitch, but a gentle giant off it". He also took part in the Lerwick Up Helly Aa.
The accident occurred on a layby between Alfreton and Ripley on the A38, with Perry's motorbike hitting a parked lorry. He was pronounced dead at the scene.