Welcome back to That Digital Take
In Season 3, Episode 2, Torri Webster sits down with Jay McCauley, one of Canada’s most influential Gen Z leaders reshaping philanthropy, corporate strategy, and political engagement in the digital age.
Jay is a strategic communications advisor, philanthropic strategist, and changemaker who has:
• Helped raise over $20 million for community causes
• Served as the youngest board member in Canadian nonprofit history
• Advised CEOs, political leaders, and major nonprofit boards
• Built a reputation for bridging Gen Z culture with legacy institutions
This episode dives deep into Gen Z leadership, purpose-driven brands, social media’s role in activism, cancel culture vs. accountability culture, youth voter engagement, and what corporations STILL misunderstand about young consumers.
If you care about impact, influence, digital culture, or building a legacy career with purpose, this is a masterclass.
What We Cover:00:00 – Meet Jay McCauley: Gen Z changemaker & philanthropic strategist
03:33 – Walking into legacy boardrooms as the youngest person in the room
04:51 – Networking honestly & building social capital
10:23 – Consulting brands on Gen Z strategy: what actually works
13:57 – Why brands get “youth marketing” wrong (and the Tate McRae debate 👀)
17:33 – Accountability culture vs. cancel culture
21:34 – Has social media permanently changed political strategy?
25:51 – Why young people MUST vote (and what’s holding them back)
33:37 – Social capitalism: Should influencers be doing more?
38:03 – Raising $20 million — what that really means behind the scenes
43:08 – Why Jay launched his podcast In Good Company
Gen Z leadership
Youth civic engagement
Purpose-driven marketing
Corporate social responsibility
Philanthropy in the digital age
Political engagement & social media
Building influence with authenticity
The future of nonprofit boards
Young entrepreneurs scaling with impact
Jay sits at the intersection of culture, commerce, and community — and this conversation feels like stepping inside a modern-day boardroom meets digital strategy lab.
This episode is for:
✔️ Founders
✔️ Creators
✔️ Marketers
✔️ Young professionals
✔️ Anyone navigating legacy spaces with new ideas
If you’ve ever wondered how to create real impact without waiting for permission — this one’s for you.
Subscribe to That Digital Take for weekly conversations at the intersection of business, influence, media, and culture.
And don’t forget to check out Jay’s podcast, In Good Company.
Leave a review if this episode resonates, it helps more listeners discover the show.
#GenZ #Philanthropy #YouthLeadership #PurposeDrivenBusiness #CorporateResponsibility #DigitalCulture #CivicEngagement #ThatDigitalTake
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