Scrymgeour worked globally as a corporate trouble-shooter before founding organisations including File Tech Inc., an information management company; The Skills Network, a group of skills training businesses; and Green Standards Ltd, an award-winning move management company that provides circular economy solutions for corporate waste that benefit both community and environment.[4]
Prior to the Rose Revolution of November 2003, he delivered political, organisational and election readiness training in the former Soviet Republic of Georgia.
In August 2004, he was hired for a dollar-per-year as an advisor to the Green Party of Canada by its leader Jim Harris.[8] In the position paper, Green and Growing, he outlined a political organization structure that emphasized minimum critical central coordination under an Executive Director and the building of volunteer-based electoral district associations.[9]
In the 2007 Ontario provincial election, he served as organisation director of the Green Party of Ontario, delivering the first full slate of 107 candidates in its history. He then served as chief financial officer from 2007-2010 and as Campaign Chair for the 2011 Ontario General Election.[10]