With more than two decades of experience in leadership development, change management, and organizational transformation, Siobhan Calderbank has become a sought-after voice in corporate leadership and diversity advancement. Her influence spans across industries and continents, having addressed audiences in over 70 countries with the aim of encouraging collaboration, inspiring action, and fostering inclusive environments.

Siobhan’s professional reach extends across several roles: she is a senior director at LCBO, a keynote speaker, a diversity practitioner, and the founder of Butterfly Ladies, a mentoring initiative aimed at uplifting women and underrepresented groups. Her thought leadership has earned her national and international recognition, along with prestigious features alongside icons like Oprah Winfrey, Maya Angelou, Deepak Chopra, and John Lewis.

As a published author and recipient of multiple awards for her contributions to equity and leadership, Siobhan’s mission remains focused on helping individuals unlock their potential and organizations cultivate spaces where everyone feels heard, seen, and valued.

From Vision to Leadership: The Spark Behind Her Journey

Siobhan’s commitment to people-first leadership began early in her career when she realized the impact of organizational change on individuals. Too often, change initiatives neglected the emotional and practical effects on teams, leading to confusion, frustration, and disengagement. Determined to shift that narrative, she set out to help leaders better navigate transformation through empathy, communication, and inclusive engagement.

Her goal was clear: become a leader who not only drives results but also empowers others to bring their authentic selves to work. Siobhan’s leadership style centers on trust, mutual respect, and creating an environment where individuals feel safe to grow and succeed.

The Birth of Butterfly Ladies: Bridging Gaps in Leadership Access

As Siobhan moved into executive roles, she noticed a recurring pattern young women, professionals, and aspiring leaders consistently reached out seeking mentorship. Many of them, especially women of color and those from disadvantaged backgrounds, shared similar concerns:

·       They saw few leaders who looked like them

·       Access to leadership development was often financially out of reach

·       Mentorship and guidance during critical life and career transitions were lacking

In response, Siobhan founded Butterfly Ladies, a no-cost mentorship platform designed to support women and youth in developing their leadership capabilities. The initiative focuses on three principles: Learn, Live, and Lead. By connecting mentees with seasoned mentors who reflect their backgrounds and experiences, Butterfly Ladies aims to build confidence, career readiness, and community-driven leadership.

Through the LeadHERship Accelerator Series, participants receive access to courses on communication, resilience, strategic thinking, personal branding, and influence all without financial barriers.

Navigating Barriers and Turning Adversity into Impact

Siobhan’s own path was not without challenges. Growing up as a Black child of West Indian heritage in a community with little diversity, she experienced bullying, exclusion, and cultural isolation. Professionally, she encountered hurdles that many women of color still face—bias, limited representation, and underestimation.

Rather than letting these experiences define her, Siobhan used them as fuel. She pursued an expansive academic journey, earning credentials in law, IT management, learning and development, project management, and change leadership. These qualifications enabled her to rise through the ranks of corporate HR and become a trusted voice in organizational strategy and inclusion.

Her resilience has become a defining trait of her leadership, inspiring others to view setbacks as stepping stones toward something greater.

Redefining Success

For Siobhan, success is deeply personal. It isn’t measured only by titles or income, but by the ability to make a meaningful impact in someone’s life. Whether through mentoring, speaking, or simply offering support, she defines success by the positive change she creates in others.

“To me, success is about alignment,” she says. “When my work, my values, and my passion come together in a way that uplifts others and brings fulfilment, that’s when I know I’m successful.”

She believes that true success encompasses wellness in all areas mental, physical, emotional, and spiritual and reflects both inner contentment and outward contribution.

Advice for the Next Generation of Women Leaders

Siobhan emphasizes the importance of building a support network early. She encourages young professionals to seek not just one mentor, but three key types of guidance:

·       A mentor to share wisdom and experience

·       A coach to provide performance feedback and growth strategies

·       A sponsor to advocate on their behalf and elevate their visibility for future opportunities

She believes that with the right guidance and a commitment to continuous learning, young women can break through barriers and create lasting influence in any field they choose.

Personal Inspiration and Values

While Siobhan has been uplifted by many mentors, colleagues, and friends, she credits her greatest source of inspiration to her mother. A model of grace, intelligence, and quiet strength, her mother instilled the values of integrity, hard work, and character lessons that continue to shape her leadership approach.

“She taught me to always give my best, even when no one is watching,” says Siobhan. “It’s not about recognition. It’s about living your values with consistency and purpose.”

Honors and Recognition

Siobhan’s impact has not gone unnoticed. Among her many accolades, she was named:

·       Top Director of the Year in Talent Management (2021)

·       Empowered Woman of the Year (2021)

·       Recipient of the Lifetime Achievement Award by IAOTP (2022)

·       One of the 100 Accomplished Black Canadian Women (2022)

·       Winner of the Women of Inspiration Award for Diversity and Inclusion (2019)

She is also a national ambassador for Black Women with the Universal Women’s Network and continues to be featured in major media outlets and international stages.

Leaving a Legacy of Empowerment

Through every role she has held, whether as an executive, author, or mentor. Siobhan Calderbank has remained focused on building a legacy rooted in equity, empathy, and empowerment. Her work is a reminder that real leadership is not just about titles or strategy. It is about helping others rise, finding strength in shared humanity, and leaving every space better than you found it.