Winston Wu is a trusted management and technology professional with over 20 years of global experience (North America, Asia and Europe) focused on helping organizations build, operate and optimize their technology infrastructure, data & analytics ecosystems, operational functions and business transformation agendas by delivering large scale business/technology programs and initiatives, and providing advisory services across various industries (financial, insurance, utilities, retail, government, health/medical and communications & high tech) in both technology and business capacities. He lives in Toronto, Canada with his wife and three children.
Recently, in an exclusive interview with CIO Magazine, Winston shared insights into his transformative journey in technology, the evolving landscape of AI and machine learning, and strategies for driving business growth through data and innovation. He also shared his personal hobbies and interests, future plans, pearls of wisdom, and much more. The following excerpts are taken from the interview.
Hi Winston. Can you tell us about your early career and what sparked your interest in technology and management?
Ever since I was a child, I was always fascinated with technology (probably stemming from video games) but upon graduating from Industrial Engineering at the University of Toronto in 2003, I joined Accenture as part of the Data Center Technologies & Operations practice. During the 7.5 years I spent at Accenture, I was immersed in the world of designing and building data centers (facilities, storage, networks, servers, HVAC, applications, security) in addition to business development, client interactions, and the management of teams and stakeholders. Additionally, I was able to work globally (across North America, Asian and Europe) which further enriched my experience.
After leaving Accenture at the end of 2010, I joined Ernst & Young (EY) in their Advisory Services practice where I was able to apply the large program transformation experience I had gained at Accenture. But, I consciously moved towards the IT Strategy and cyber security domains as I saw the increasing interest in these two areas from organizations across all industries. Before I left EY after 5.5 years, I was hyper focused in mergers & acquisitions helping clients integrate their technology and business functions and ecosystems to realize synergies.
I would say my 13 years in global consulting further reinforced my natural work ethic and discipline but definitely enabled me to expand my knowledge and skills given the exposure to various technologies and challenges across numerous clients across multiple industries (banking, insurance, wealth management and capital markets, health, public sector, utilities, retail, commercial development, fleet management).
I left the consulting world and joined one of the largest Canadian banks in late 2016 which is when my journey with data & analytics and data science began. It’s been around 10 years now that I’ve been in this space across banking, insurance, telecommunications, software/product and healthcare, and there is no shortage of excitement with the continuous evolution of technology, the growing landscape of challenges to solve and the ever-increasing adoption and applicability of AI.
What do you love the most about your current role?
There are several dimensions I love about my current role but the top three would have to be: 1) The types of challenges we get to tackle from a technology and use case perspective; 2) The people that I get to work with due to their diverse personalities, experiences and personal backgrounds; and 3) The mission of the organization as a whole.
How do you see the role of AI and machine learning evolving in the next 5-10 years, and what opportunities and challenges do you think it will bring for organizations?
I see it as an algorithmic transformation because AI is transforming data and signals, problems, business processes and people. The primary opportunity with AI is when AI acts as an augmentation tool, freeing workers for high-value activities: critical thinking, creative problem-solving, innovation, and strategic oversight. The main challenge will be related to algorithmic bias which is why Responsible AI should be on top of mind of any organization looking to leverage AI – this drives the need to ensure there are mechanisms to test for bias, toxicity, accuracy, etc. in addition to intentional design and human-in-the-loop oversight.
What are some of the most important qualities or skills you think a technology leader should have, and how can they develop them?
I would consider five key areas:
- Strategic and Business Acumen (connecting technology investments directly to business value and long-term strategic goals) – Study market trends, understand company KPIs (Key Performance Indicators), and focus decisions on measurable business outcomes, not just technical merit.
- Communication and Stakeholder Management (translating complex technical concepts for non-technical audiences and practicing active listening) – Practice tailoring presentations to different audiences, focusing on business impact over technical detail.
- Adaptability and Change Management (guiding teams through rapid technological and organizational change) – Embrace Agile methodologies, practice scenario planning, and lead by example in adopting new technologies.
- People Management and Coaching (building diverse, high-performing teams through trust, delegation, and coaching) – Improve Emotional Intelligence (EQ), delegate meaningful work, and prioritize staff career development in one-on-ones.
- Technical Competence (maintaining enough depth to make informed architectural decisions, to assess risk, and to earn team respect) – Participate in key architectural reviews, dedicate time to continuous learning about emerging technologies, and stay connected to the team’s daily challenges. Always be curious.
Can you share a book or resource that inspires you and why?
I came across the book “Hustle and Float: Reclaim Your Creativity and Thrive in a World Obsessed with Work” by Rahaf Harfoush when I heard her speak at a data & analytics conference in London, UK in 2025. The message and book is inspiring to me because it challenges the pervasive and often destructive culture of “hustling.” The key inspirational takeaways center on a more humane and sustainable approach to work and creativity –
- The realization that endless hustling – working harder, faster, and longer – is often counterproductive to true creativity and is actively damaging to mental and physical health.
- The power of “Float” encourages embracing the concept of “floating,” which represents the essential periods of rest, recovery, and deep focus needed for creative breakthroughs. The inspirational message here is that stepping away, reflecting, or even resting is not laziness; it is a vital, non-negotiable part of the creative process.
- Inspires readers to question the deep-seated cultural and historical belief that one’s worth is solely tied to constant, measurable productivity. This is an emancipating message that frees people from the pressure to constantly be “on” and producing.
- Ultimately, the book points toward a path to a more humane, sustainable, and genuinely creative way of living. It offers hope that you can thrive in the modern knowledge economy without burning out or compromising your values.
It is important to emphasize that “not hustling” is not the message here – working hard will always be core to success but there needs to be a balance with the ability to give oneself the space to reflect and think.
What is your favorite quote?
“You can’t do anything about the past, you can only operate in the present and plan for the future.” – Jamie Dimon
I choose this quote because I genuinely believe in focusing on what one can control, and personal drive and perseverance and because of a high level of respect for Mr. Dimon and his career.
What are some of your passions outside of work? What do you like to do in your time off?
Like many of my peers who have very busy work schedules, what I do with my personal time has to be very selective – Most of my personal time is spent with my wife and children, traveling, spending time with friends, volunteering and mentoring.
What is your biggest goal? Where do you see yourself in 5 years from now?
I aspire to be a CIO, CTO or Chief Transformation Officer where I am able to drive influence and impact across multiple lines of businesses and play a role in shaping the future of an organization.
What advice would you give to young professionals looking to start their career in technology and management?
With AI’s impact on our economy and society, I would recommend that young professionals focus on Technical Fluency, Critical Thinking, Ethical Awareness and Continuous Learning. I would also encourage them to seek mentors in their professional and personal networks – real world experience from various perspectives will always be invaluable. And lastly, developing deep specialized expertise in niche domains and building portfolios demonstrating competencies through real-world projects will also help differentiate themselves.