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] Scrymgeour held the position of national director of the Progressive Conservative Party of Canada under former Prime Minister of Canada Joe Clark from 2002–03, resigning as part of the deal between David Orchard and Peter MacKay that led to MacKay's assumption of leadership and caused a storm of protest within the party.

Prior to the Rose Revolution of November 2003, he delivered political, organisational and election readiness training in the former Soviet Republic of Georgia.

[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.

[10] Scrymgeour has acted as an advisor, donor and/or board member for organizations including Venture for Canada, MaRS Discovery District, One Laptop per Child, the Belinda Stronach Foundation, the Canadian Executive Service Organization, Oak Ridges Moraine Land Trust, Anglican Church of Canada and the Make Poverty History Campaign.