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Rob “Happy” Gilmour
Partner at Crestview Strategy
Rob "Happy" Gilmour is a Partner at Crestview Strategy, a public affairs and strategic communications firm based in Toronto, Ontario, Canada.12 He has over twenty years of experience in various aspects of public affairs, including stakeholder relations, communications, training, public relations, events, fundraising, and campaign leadership.1
Career Highlights
Government Experience:: Gilmour has worked on Parliament Hill and at Queen's Park for two progressive conservative governments.1 He previously served as a deputy executive director at PC Caucus Services, where he oversaw research, outreach, and political affairs for the Ontario PC Government Caucus.1
Political Campaigns:: He has served in senior roles on successful leadership, central, and local campaigns.1 Gilmour is often asked to organize, present, or train candidates and attendees at political conventions.1
Private Sector Experience:: Prior to joining Crestview Strategy, Gilmour held positions at various organizations:
- Vice President at Counsel Public Affairs Inc.
- Senior Vice President at The Daisy Group
- Principal Consultant at Profile Public Affairs Inc.
- Senior Consultant at Hill+Knowlton Strategies
- Manager of Sponsorship and Fundraising at Ontario Bar Association1
Expertise
Gilmour's areas of expertise include:
- Provincial politics
- Labour and union issues
- Stakeholder relations
- Communications strategy
- Fundraising
- Campaign management12
Notable Achievements
- Co-authored a political fundraising manual
- Launched three successful sponsorship departments
- Helped raise over $10 million in various roles
- Led a campaign that earned 89 municipal council resolutions of support from 42 separate Ontario municipalities during a six-week period1
Rob "Happy" Gilmour joined Crestview Strategy as a Vice President in December 2021 and was promoted to Partner in May 2024.14 His LinkedIn username is indeed gilmourrob.3
