What separates marketing that looks impressive from marketing that creates measurable business growth?

In this episode of Success Leaves Clues, Robin and Al sit down with Alison Simpson, recently retired President and CEO of the Canadian Marketing Association, to explore marketing leadership, brand and culture alignment, business transformation, career growth, and the courage to act before certainty arrives.

Alison explains why marketing leaders must speak the language of revenue, profit, customer lifetime value, and market share if they want to influence business strategy. She shares how a customer growth strategy at Holt Renfrew contributed to a 21% annual sales increase and attracted 270,000 loyalty program members in its first year.

The conversation also explores the subtle language that reveals when employees no longer feel connected to a brand, why leaders build trust by taking responsibility when something fails, and how accountability can strengthen psychological safety throughout an organization.

Drawing on a career that has spanned agency leadership, iconic brands, startups, corporate marketing, and the Canadian Marketing Association, Alison shares the principles that shaped her success: say yes when you are 70% ready, choose clarity over certainty, build relationships before you need them, and treat your career as a landscape rather than a ladder.

She also reveals what completing 65 marathons and ultramarathons taught her about preparation, resilience, ego, and the essential difference between something that is hard and something that is harmful.

You’ll hear about:

• How employee language reveals a growing divide between brand and culture
• Why customer-facing employees are critical to delivering a brand promise
• How leaders build trust by publicly taking responsibility for mistakes
• Why marketing needs more than a symbolic seat at the leadership table
• How to translate marketing activity into measurable business outcomes
• The strategy that helped generate a 21% annual sales increase at Holt Renfrew
• Why 70% certainty can become a competitive advantage
• How to distinguish relationship-building from collecting contacts
• What endurance racing teaches leaders about preparation and resilience
• Why ambition, kindness, and integrity are not competing priorities
• How Alison became the first female CEO in the CMA’s history
• Why the strongest careers are landscapes rather than ladders

We talk about:

00:00 Al’s Great Cycle Challenge for SickKids

01:13 Meet Alison Simpson and her unconventional career journey

03:23 How Alison became an endurance athlete

05:01 Running 250 kilometres across the Sahara Desert

06:39 The early warning signs of brand and culture misalignment

09:00 Experiencing the customer journey before leading the team

12:45 How accountability builds trust throughout an organization

16:43 Why marketing still fights for strategic influence

18:05 Speaking the language of revenue, profit, and business growth

24:04 How businesses can measure marketing ROI

26:14 Rewirement and saying yes before you feel ready

31:08 Travel, meaningful experiences, and a priceless family memory

35:11 Is this hard, or is it harmful?

41:22 Ambition, integrity, and building a career without a ladder

Connect with Alison

• LinkedIn: https://www.linkedin.com/in/alisonksimpson/

Connect with Us

• LinkedIn: Robin Bailey and Al McDonald
• Website: Aria Benefits and Life & Legacy Advisory Group