In this episode of Success Leaves Clues, host Robin Bailey and co-host Al McDonald sit down with Connor Bays, Head of Sales and Partnerships at Common Wealth Retirement, to explore how technology, inclusion, and purpose are reshaping financial wellness and the future of retirement. 

Connor shares his journey as a competitive runner turned mission-driven leader helping Canadians achieve lifelong financial security. Through his work at Common Wealth, he’s redefining how small and mid-sized businesses can offer accessible, high-impact retirement plans that support employee wellbeing and retention. 

Together, they dive into the realities of financial stress, the misconceptions about cost and complexity in group retirement programs, and the profound shift from viewing retirement as an ending to embracing it as a new beginning. 

This conversation blends insight and empathy, showing how small changes in how we save, educate, and communicate about money can spark long-term transformation, for both employees and employers. 

You’ll hear about: 

• Mission-driven innovation: How Common Wealth is closing the retirement gap for Canadians. 
• Financial accessibility: Why smaller businesses can and should offer group retirement benefits. 
• Common misconceptions: Breaking down the myths around cost and complexity. 
• Financial stress and wellbeing: How retirement planning contributes to mental and emotional health. 
• Engaging younger generations: Why millennials and Gen Z care deeply about their financial future. 
• Technology meets trust: Using digital tools to personalize financial planning at scale. 
• Redefining retirement: From an end point to a new phase of meaning, purpose, and contribution. 
• Employer wins: Why group retirement plans are a competitive advantage for engagement and culture. 

We talk about: 

• 00:00 Introduction   
• 03:00 From competitive running to leading at Common Wealth 
• 04:00 How Common Wealth is closing Canada’s retirement gap 
• 06:00 The biggest barriers to offering group retirement plans 
• 09:00 Financial literacy and breaking the taboo around money 
• 10:00 Retirement planning as part of overall wellbeing 
• 12:00 How younger generations are engaging with retirement savings 
• 15:00 Making financial confidence accessible through technology 
• 18:00 Balancing fees, service, and meaningful financial outcomes 
• 20:00 Personalization in benefits: what employees truly want 
• 22:00 The evolution of retirement: purpose, health, and longevity 
• 25:00 The psychology of retirement and identity beyond work 
• 27:00 Wins for employers heading into 2026: new and upgraded plans 
• 30:00 Planting trees for future generations through better access and education 

Connect with Connor 

• LinkedIn: https://www.linkedin.com/in/connorbays  
• Website: https://www.commonwealthretirement.com/  

Connect with Us 

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