In this episode of Success Leaves Clues, hosts Robin Bailey and Al McDonald sit down with Cheryl Kerrigan, award-winning Chief People Officer at BlueCat and one of Canada’s most admired HR leaders. With more than two decades of global experience, Cheryl shares her journey of stepping into roles before she felt “ready,” embracing failure as a teacher, and shaping workplace cultures where people and performance thrive.
You’ll hear about:
- The power of courage and curiosity: Why putting your hand up before you’re fully prepared can accelerate growth.
- The role of mentorship: How strong leaders and female role models shaped Cheryl’s career, and why she’s passionate about sending the elevator back down.
- Building high-performing teams: From over-communicating strategy to enabling leaders with coaching and development.
- Supporting resilience in tech: Wellness days, flexible policies, and innovative benefits that prioritize employee well-being in a fast-paced industry.
- Planting future trees: Why Cheryl is committed to connecting new graduates with opportunities and helping the next generation step confidently into business.
If you’ve ever struggled with imposter syndrome, wondered how to foster a culture where people truly thrive, or wanted practical insights from one of Canada’s top HR leaders, this episode is filled with clues you’ll want to follow.
We talk about:
- 00:00 Introduction and Podcast Overview
- 04:15 Cheryl's Career Journey and Leadership Insights
- 11:31 Building High-Performing Teams
- 15:35 Balancing Business Growth and Employee Well-being
- 21:10 Innovative Employee Benefits and Support
- 25:07 Future Trends in Employee Benefits
- 30:24 Cheryl's Mentorship and Giving Back
- 33:19 Conclusion and Contact Information
Connect with Cheryl
Connect with Us
• LinkedIn: Robin Bailey and Al McDonald
• Website: Aria Benefits and Life & Legacy Advisory Group
