Siobhan Calderbank

“When you have better leaders, you get better team members who are more engaged, and they give that discretionary output.”

Siobhan Calderbank can now produce in a few hours a training program that once took roughly 40 hours to build, yet she insists that speed only matters if the person behind it knows what excellent looks like. As Vice President, Talent and Performance Management at Element Fleet Management, the Toronto-based fleet management company, she oversees the systems that shape how people grow, lead and perform: talent development, performance management, succession planning, leadership development and learning.

Her remit stretches further than most. Sales training, which typically sits under sales enablement within marketing, communications or the commercial side of a business, now falls within her portfolio at Element. It is a new arena for her, and one she has taken on with the same conviction that has guided her career: develop better leaders, and everything downstream improves.

"When you have better leaders, you get better team members who are more engaged, and they give that discretionary output," Siobhan says. Nearly every chapter of her career, from training and development to change management to executive HR leadership, traces back to that idea.

A Teacher's Daughter Finds Her Field

Learning runs in the family. Siobhan's mother is a teacher, and Siobhan grew up imagining she might follow in those footsteps. The route there was indirect. Her first post-secondary studies were in law, and while she found the subject engaging, she concluded that legal practice, whether as a paralegal or a lawyer, was not where she wanted to spend her career.

She moved on to a degree in IT, and by the end of her second year she knew that fixing computers and managing technology were not her calling either. Rather than abandon the program, she finished it and filled every elective slot with training courses. Those were the classes she loved. After graduating, she stayed one more year to complete a certificate in training and development, then joined a training and development team.

She quickly noticed that many training programs are essentially small projects, so she added a certificate in project management and earned her PMP. That combination of instructional design and disciplined execution carried her into consulting for a couple of years, where she worked across training and development, leadership development and change management.

Climbing Deeper Into HR

From consulting, Siobhan stepped into a director role in change management, then became a director of learning and development. Her move into talent management marked a deeper leap into HR, adding performance and succession disciplines to the learning work she already knew well.

She broadened that experience by leading a retail learning program spanning 680 stores across Ontario. From there she rose to HR vice president, widening her responsibilities across the people function. Her motivation has stayed constant through each promotion. She describes her work as a form of service: making sure people get what they need to become the best versions of themselves.

Mentors Who Widened the Stage

Three leaders, each with a distinct style, shaped her path. Early in her career, Priscilla took Siobhan under her wing, and by coincidence the two went on to work together at more than one organization. Priscilla showed her the processes, policies and practical mechanics of getting things done, and pushed her to grow her expertise in learning and development exponentially, along with her capacity as a leader.

In consulting, she worked with Gregg Brown, the change-management expert, keynote speaker and author. His lesson was to use her voice. He encouraged her onto bigger stages, including keynote speaking, and opened doors to opportunities she says she would not otherwise have had. Both Priscilla and Gregg continue to mentor her today.

Her current leader, Bill Sutherland, Chief People Officer at Element Fleet Management, brought yet another style and a steady confidence in her ability to deliver. His faith in her is what placed sales training under her portfolio, exposing her to an entirely new discipline and sharpening a skill set she continues to expand.

AI as an Amplifier, Not a Substitute

Siobhan is an unambiguous advocate for embracing AI. That shift from 40 hours to a few hours is only part of the story: a passable first draft can now appear in 15 to 20 minutes. Her teams pair tools such as Articulate and Rise with ChatGPT to shape program outlines, write content and design graphics and activities, work that was far harder a decade ago.

She is equally clear about the limits. Without foundational expertise, she argues, AI produces C-level work, not an A game. Professionals still need to know their craft; the tool then makes them faster and lets the best performers shine brighter. Those slow to adapt risk being left behind.

Her change management background shapes how she views adoption. Resistance is predictable, she notes, just as some people once resisted electricity. The task for leaders is to reduce that resistance and integrate AI into daily work, because it is here to stay.

Advice for Talent Leaders: Keep It Human

For all her enthusiasm about digital tools, Siobhan's advice to fellow talent leaders centers on people. As organizations ramp up their digital proficiency, she urges them not to lose sight of human connection. Empathy, thoughtful coaching and attention to nuance will be extremely important. AI can only do so much, she says; people are the ones connecting all the pieces.

Belonging, she adds, cannot live only in an email or a polished diagram. People can feel when they are genuinely connected to another person. They want leaders who can look them in the eye, demonstrate care and concern, and show that they value who they are and the perspective they bring.