David Daigle
Founder & Chief Strategy Officer @Wingman Dx
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WORK HISTORY
Founder & Chief Strategy Officer @Wingman Dx
Calgary, FR
Wingman DX operates as a strategic co-pilot for organizations navigating growth, digital transformation, and brand evolution. The firm aligns digital strategy, marketing architecture, and brand positioning into a clear and executable flight plan designed to support sustainable growth.Engagements typically include:• digital strategy and transformation roadmaps• fractional marketing leadership• brand and positioning strategy• marketing infrastructure and systems design• growth strategy for owner-led and family businessesLeadership approach informed by training through the Disney Institute in leadership excellence, employee engagement, and service design.Typical Engagements.Organizations usually reach out when they are navigating one of the following moments:• Growth has outpaced marketing strategy and leadership needs clearer direction• A family business is preparing for generational transition or modernization• Digital investments feel reactive rather than strategic• Marketing exists, but positioning and brand clarity are weak• Leadership teams want executive-level marketing leadership without hiring a full-time CMOEngagements typically take the form of strategic advisory, fractional leadership, or focused strategy development.
EDUCATION
Mount Royal University
Bachelor, Communications
Mount Royal University
Diploma, Computer Information Systems
SKILLS
ABOUT DAVID DAIGLE
Most businesses don’t struggle because of effort. They struggle because of clarity.That’s where a Wingman comes in.After years working alongside entrepreneurs and owner-led organizations, I’ve seen the same pattern repeat itself. Strong companies often reach a point where growth outpaces strategy — marketing becomes fragmented, digital investments feel reactive, and leadership teams start asking bigger questions about positioning, technology, and direction.As the founder of Wingman DX, I work alongside small and mid-sized organizations as a digital strategy advisor and fractional marketing leader, aligning brand, marketing, and digital infrastructure into a clear and executable flight plan for growth.My work typically focuses on:• digital strategy and transformation• marketing and brand strategy• growth architecture for SMEs• fractional CMO leadership• family business modernization and transitionMy leadership perspective is also shaped by training through the Disney Institute, exploring how culture, service design, and leadership architecture contribute to enduring organizations.Beyond consulting, I remain actively involved in mentorship and community leadership. I’ve served as a mentor through Mount Royal University’s Mentorship Program since 2017, supported entrepreneurs through Higher Landing, and worked with newcomers through the Calgary Catholic Immigration Society.In 2024, this work was recognized with the Desjardins GoodSpark Award for Community Development.Where I typically engage.Most conversations that land on my desk involve organizations navigating one of these moments:• A business growing faster than its marketing strategy• Leadership teams unsure where digital investments should actually go• Family businesses preparing for generational transition• Companies with strong products but unclear market positioning• Organizations modernizing operations through digital and AI-driven systemsThese engagements typically take the form of strategic advisory work, fractional leadership, or focused strategy development.Conversations I enjoy:• Business owners navigating their next stage of growth• Family enterprises planning succession or modernization• Organizations rethinking their digital strategy• Students and emerging professionals exploring careers in strategy, marketing, and entrepreneurshipFounder of Wingman DX — a digital strategy consultancy based in Calgary.
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