Every year, Canadian organizations lose roughly $30 billion to technology waste, project failures, and cyber breaches. Drawing on decades of technology leadership experience and the latest research, this program reveals a consistent pattern: when technology fails, it almost always traces back to one of five predictable mistakes.
In this session, Nancy MacKay moderates a conversation with Charlie Feld and David Trent on the five things CEOs need to get right before making significant bets on any technology including AI.
What You’ll Walk Away With
- A clear lens for assessing your organization’s readiness for Technology
- The most common failure points in large-scale transformation
- Practical insight into aligning your leadership team and operating model
- A framework for making better technology investment decisions
- A sharper understanding of where to focus in the next 90 days
Who Should Attend
CEOs, Executives, and Business Owners navigating:
- AI and digital transformation decisions
- Organizational change and scaling complexity
- Leadership alignment and execution challenges
About our Panel
David Trent, Founder, Technology Done Well | Forum Chair, MacKay CEO Forums
David Trent brings more than 30 years of experience leading technology, digital innovation, and enterprise transformation across complex, asset-intensive organizations. His career has been defined by translating strategy into measurable business outcomes ensuring that technology investments deliver real operational and financial impact.
He has held senior executive roles at Canadian National Railway, where he served as Chief Digital Officer and Vice President of Operating Technologies, and at Canadian Forest Products, where he was Senior Vice President of Business Development and Senior Vice President of Supply Chain and Digital. Earlier in his career, he held leadership roles at Methanex and Intrawest, consistently driving performance improvements through disciplined execution.
As Founder of Technology Done Well, David works with boards and executive teams to plan, implement, and operate technology effectively, with a focus on governance, accountability, and long-term value creation.
David holds a Bachelor of Arts in Economics from Simon Fraser University and earned his CPA CMA, graduating top of his class. He is also an Accredited Board Director with the Chartered Governance Institute of Canada and has served on multiple boards, including Railinc and Canada’s Digital Supercluster.
Charlie Feld, Founder, Feld Group Institute | Former CIO & Transformation Leader
Charlie Feld is a recognized leader in large-scale business and technology transformation, with a career spanning more than four decades advising global organizations on how to execute complex change successfully.
He is the Founder of the Feld Group Institute, where he works with CEOs and executive teams to align business strategy, operating models, and technology investments to drive sustained performance. His work focuses on helping organizations move beyond fragmented initiatives to achieve integrated, enterprise-wide transformation.
Earlier in his career, Charlie served as Chief Information Officer at companies including Frito-Lay and Burlington Northern Santa Fe, where he led major modernization efforts and operational improvements. He has since advised many of the world’s leading organizations across industries, bringing a practical, execution-focused approach to transformation.
Charlie is also the author of Blind Spot: A Leader’s Guide to IT-Enabled Business Transformation, which outlines a structured framework for aligning leadership, operating models, and technology to achieve measurable results.
About our Moderator
Nancy MacKay, Founder and CEO | MacKay CEO Forums
Nancy MacKay is the founder and CEO of MacKay CEO Forums, an organization that provides the highest impact and least time-intensive peer support groups for over 1,300 CEOs, executives, and business owners across Canada and around the world. Since founding MacKay CEO Forums in 2005, Nancy has been dedicated to fostering inspiring leadership through confidential peer learning and support. Under her leadership, MacKay CEO Forums has built a community of over 1,300 members, facilitated by 60+ Forum Chairs, delivering an ROI of 708% through increased profit, employee retention, and customer satisfaction as measured by the ROI Institute Canada in 2022.
A seasoned CEO coach, dynamic keynote speaker, former university professor, and Forbes-published author, Nancy draws on more than two decades of experience working with thousands of CEOs. Her latest book, It’s Lonely at the Top: CEO Strategies for Inspiring Yourself and Your Team, published by Forbes Books, is an Amazon Kindle bestseller across multiple categories. The book offers a practical and candid look at the realities of leadership at the top, and the importance of self-leadership and peer support in sustaining high performance.
Nancy is also the co-author of I Don’t Have Time, with Nico Human, which addresses the most common time mastery challenges CEOs face, as well as two influential books with Alan Weiss: The Modern Trusted Advisor and The Talent Advantage.