Keynote Speakers for Small Business Week
Voices of Entrepreneurship: Keynote Speakers for Small Business Week
October’s Small Business Week is a timely opportunity to celebrate the founders and risk-takers innovating the economy forward. For your upcoming workshops, client networking events, or lunch-and-learns, deliver the forward-looking insights that empower your entrepreneurial attendees to navigate the changing market ahead.
Here are five voices worth bringing to your next Small Business Week event.
In this post:
- Fenton Jagdeo Jr. — L’Oreal acquired founder and creator of “Curiosity Compass” framework for innovation
- Bobby Umar — Personal branding and digital influence for entrepreneurs
- Kristen Gale — Franchising, international scaling strategies, and turning setbacks into success
- Arlene Dickinson — High-stakes entrepreneurship, investment, and driving growth
- Dr. Chitra Anand — Intrapreneurship, innovation, and ESG
______
1. Fenton Jagdeo Jr. — Innovation and Radical Curiosity
Fenton Jagdeo Jr. brings a rare combination of startup execution, Deloitte consulting, and civic leadership to the stage.
His proprietary Curiosity Compass framework — built from over a decade of hands-on work with Fortune 500s, high-growth startups, and billion-dollar public boards — gives audiences a practical framework for challenging assumptions, borrowing ideas across industries, and turning uncertainty into competitive advantage. His former company, Faculty, was acquired by The Estée Lauder Companies, and he holds a historic appointment as the youngest director ever named to the Toronto Transit Commission board.
Sample audience review: “Fenton was an absolute pleasure. So very personable and knowledgeable. He is very intriguing to listen to, and the hour just flew by. I honestly couldn’t believe it went so quick, I could have listened to him speak much longer :)”
— Senior Manager, National Conferences and Events, Habitat for Humanity Canada
Best For: Forward-looking teams in innovation and growth mode, building curiosity into their team’s practice
2. Bobby Umar — Brand Building & Digital Influence
Bobby Umar is recognized by Inc. Magazine as one of the Top 100 Leadership Speakers in North America — His message is especially high-value: your personal brand is your most underleveraged business asset.
A five-time TEDx speaker, LinkedIn Top Voice with 50,000+ followers, and author of a #1 bestseller, Bobby helps founders and entrepreneurs understand how to build authentic digital presence and turn their story into influence. His sessions are high-energy, interactive, and immediately actionable — with a background spanning brand marketing at Kraft and Unilever, engineering at Bombardier, and performing arts training at Second City, he brings unique depth to the entrepreneurship stage.
Sample audience review: “Bobby’s insights into our business and the way we operate were bang on. Can’t wait to have him back!”
— Marketing Director, PepsiCo
Best For: Entrepreneurs and small business owners who want to grow their visibility, own their digital presence, and turn authentic storytelling into a growth engine
3. Kristen Gale — Scaling with Grit
Kristen Gale built THE TEN SPOT® Beauty Bar from a single Toronto location into an internationally recognized franchise brand — and she’ll tell you exactly how the setbacks shaped the success.
Named Canada’s Top 40 Under 40, a multiple-year Profit Magazine 500’s fastest-growing company, and recognized by Entrepreneur Magazine’s Top Global Franchises, Kristen’s story is a masterclass in tenacity, brand-building, and knowing how to pivot.
Keynote highlight: From Fired to Founder to Franchisor — her riveting, candid account of early setbacks and the path to international scale
Best For: Entrepreneurs and small business owners building for growth, exploring franchising, or navigating the messy middle of scaling
4. Arlene Dickinson — The Core Strategies for Growth
Arlene Dickinson‘s relevance to today’s entrepreneurial landscape is sharper than ever.
A Dragon for over 17 seasons on CBC’s Dragons’ Den, Arlene’s perspectives on securing investment, navigating risk, and building a business that endures is grounded in real stakes. She speaks directly to what founders are facing right now — a shifting economic environment, new pressures on Canadian business, and the critical importance of resilience and strategic clarity. Her keynote is less inspiration and more activation: here is what the market demands, here is what investors look for, here is how you position your business to win.
Sample audience review: “Arlene Dickinson’s personal story was a wonderful way to start the day — her emphasis on dimensions of character not often discussed, such as humanity and humility, was particularly powerful.”
— Ivey Business School
Best For: Growth strategy, investment readiness, and building businesses built to last in today’s economy
5. Dr. Chitra Anand — Intrapreneurship, Innovation, and Building from the Inside Out
Dr. Chitra Anand on Intrapreneurship, Creativity and Entrepreneurial Thinking
Chitra explores how Intrapreneurship can be used as a gateway for organizations to achieve sustainable innovation.
A former Microsoft Canada executive, Globe and Mail Top 50 Changemakers honoree, and author of The Greenhouse Approach — a required read in the Forbes School of Business MBA program — Dr. Anand draws on 20+ years as an executive in the technology sector. Her work on intrapreneurship, ESG, and creative thinking is particularly well-suited for business audiences navigating questions of disruption, innovation culture, and long-term sustainability. In 2024, she was awarded the Smart Speakers Best of the Stage Award for her work on AI and innovation.
Sample audience review: “The positive reaction was overwhelming. Chitra’s experience and research were presented in the best possible way to open our eyes on what it will take in the coming years to be successful both as an organization and as an individual.”
— CEO, MTY Group
Best For: Organizations and business associations looking to inspire innovation culture, intrapreneurial thinking, and responsible growth with an ESG lens
Book a Speaker for Your Small Business Week Event
NSB represents some of Canada’s most compelling entrepreneurship and business keynote speakers — and we’ve been matching Canadian organizations with the right voices for over 50 years. These speakers are available through National Speakers Bureau, Canada’s original speakers bureau.
Whether you’re building a half-day workshop, a luncheon keynote, or a full conference program for Small Business Week, our team can help you find the right fit for your audience, your budget, and your goals.
Contact NSB today to get personalized recommendations for your next entrepreneurship or small business event.