Rob “Happy” Gilmour is a Vice President with Crestview Strategy based in Toronto.
Happy’s expertise encompasses provincial politics, labour, union issues, transportation, municipal and community relations, accessibility, and the not-for-profit sector. As a sought-after presenter, trainer, and political organizer, he brings over 20 years of public affairs, crisis communications, start-up, and campaign experience. With a passion for people and public affairs and having held senior leadership roles on countless election campaigns, he is dedicated to his clients’ success.
Happy most recently worked as Vice President for a national consultancy and at Queen’s Park as the Deputy Executive Director of PC Caucus Services. He oversaw research and political operations for the Ontario PC Caucus and has worked on Parliament Hill and at Queen’s Park. Rob has overseen the creation of three sponsorship departments and helped lead the growth of a national car-sharing and technology start-up company from launch to thirty-four markets across Canada. As an experienced coalition-builder, Rob is a former Executive Director of an association dedicated to accessibility rights. He also spends time assisting a Canadian Paralympic gold medalist and the world’s best trick golf entertainer in their ongoing push for inclusion and accessibility advocacy.
Happy graduated as the president of his university and high school student unions, played a leadership role in launching a national charity in Niagara and has knocked on over 30,000 doors for rural and urban Progressive Conservative candidates.
Happy currently serves on the Board of Governors for George Brown College and advisory board for ParaGolf Canada. He earned a bachelor’s degree in English Language and Literature from Brock University and grew up on a turkey farm in the heart of the Niagara Region.