I recently had the opportunity to sit down with Glen McCracken, Head of Data Analytics and Automation at the billion-dollar fintech giant ION Analytics.

Glen’s career traces the evolution of data science and technology over several decades. However, what stood out most during our conversation were his candid insights on AI, leadership, and the untapped potential of unstructured data.

The Beginnings of a Data-Driven Career

Glen’s journey began with an undergraduate degree in statistics and corporate finance, followed by a short period working in actuarial science. It was a path he quickly realised wasn’t the right fit.

His career trajectory shifted when he joined PricewaterhouseCoopers, where he worked on data-centric projects including forestry valuation models and spam filters for Yahoo. These early experiences provided a crash course in the power of data and its wide-ranging applications.

However, it wasn’t until Glen led the creation of a new technology infrastructure at Eden Park for the 2011 Rugby World Cup that his perspective on digital transformation truly evolved.

This project went far beyond simply implementing technology. The objective was to achieve two critical outcomes:

Both were essential to the success of the tournament.

The project also highlighted the importance of building systems that could be centrally managed by a single operator, rather than relying on a large IT team. This experience expanded Glen’s understanding of how data and automation could integrate into everyday operations and strategic decision-making.

What began as a focus on statistics and modelling evolved into a broader vision for how data, automation and AI could enhance operational efficiency on a global scale.

This pivotal project ultimately led to an invitation to work on the 2012 Olympic Games in London, taking Glen from New Zealand to the centre of global technological innovation.

Integrating a Tidal Wave of Data

After relocating to London nine years ago, Glen joined ION Analytics. Rather than easing into the role, he was immediately given a monumental challenge.

The task: merge the datasets of multiple billion-dollar companies.

Naturally, I asked how anyone even begins tackling such a problem.

Glen laughed.

“It was actually four companies.”

The scale of the project was staggering.

“We were dealing with over 50 different systems across these companies, each with its own complex tech stack.”

The strategy Glen adopted was unconventional.

Rather than starting with the easiest integrations, the team tackled the most complex problem first.

“When you start with the hardest integration, you learn the most. If you start with the easier ones, you often have to go back and redo everything once you encounter the complex problems.”

By solving the toughest challenge first, Glen’s team created a foundation that allowed the remaining integrations to move much faster.

“Once we cracked the first one, we were able to handle the other three integrations simultaneously. It actually ended up being smoother than we expected.”

The Changing Face of Leadership

Our conversation naturally turned to leadership.

In the context of the recent wave of high-profile executive departures, sometimes referred to as the “Big CEO Exodus,” Glen offered a thoughtful perspective on the changing demands placed on leaders.

He described two distinct leadership archetypes.

The first are what he calls “master orchestrators.”

These are leaders like Elon Musk and Jeff Bezos, who break problems down to their fundamental components using a first principles approach.

The second group are leaders who have climbed the corporate ladder by mastering existing systems and processes.

While this experience is valuable, Glen believes it can sometimes slow decision-making in periods of rapid technological change.

“These leaders often rely on how things have always been done. That can make it harder to adapt when the industry shifts.”

In contrast, the next generation of CEOs will need to operate differently.

Glen believes the future belongs to “master facilitators.”

These leaders will:

Rather than specialising in a single discipline, they will understand how different technologies interact across the entire organisation.

As AI, automation and large-scale data systems continue to reshape industries, boards will increasingly look for leaders who are comfortable navigating technological complexity.

The Untapped Power of Unstructured Data

As the discussion moved towards artificial intelligence, one theme kept returning: unstructured data.

While much of the current AI conversation focuses on structured datasets, Glen sees far greater long-term potential in data that has historically been harder to analyse.

“Think about churn prediction models,” he said.

“Right now they focus mostly on behavioural and firmographic data.”

However, organisations possess enormous quantities of unstructured information, including:

When analysed correctly, this data can offer powerful insights into customer behaviour and organisational performance.

But Glen was quick to highlight the biggest obstacle companies face.

Data quality.

“Every company wants AI. But AI is only as good as the data it runs on. You can’t build a house on unstable foundations. Bad data means bad AI.”

For Glen, the real challenge is not simply collecting more data, but ensuring it is accurate, relevant and properly integrated.

If organisations can solve that problem, the possibilities become extraordinary.

“Imagine salespeople freed entirely from admin tasks. AI could automatically generate CRM updates, call summaries, meeting notes and highlight customer feedback.”

The Unexpected Rise of a LinkedIn Personality

Glen’s LinkedIn presence has developed something of a cult following.

Naturally, I asked how it started.

His answer was refreshingly honest.

“It began as a way to vent.”

At a private equity event in Austin, a young speaker confidently claimed that AI began in 2020.

That comment didn’t sit well with Glen.

Frustrated by what he saw as a lack of historical perspective, he posted his thoughts on LinkedIn.

The response was immediate.

What began as a single post turned into a year-long series of candid, humorous observations about the tech industry.

For Glen, writing became both a way to share knowledge and a form of therapy.

Looking Ahead: Personal AI

Towards the end of our conversation, Glen’s excitement about the future of AI became particularly clear when discussing personal AI systems.

He referenced recent conversations between Sam Altman and Mark Zuckerberg about the potential for AI assistants that can operate continuously in the background of daily life.

Glen is so intrigued by this concept that he plans to experiment with the Limitless Pendant, a wearable device designed to record conversations, generate notes, and summarise daily activities.

The vision is a form of digital memory, capable of enhancing productivity and decision-making.

However, Glen also explained why AI adoption is progressing more slowly than many expected.

“The biggest obstacles right now are privacy concerns, opaque algorithms and the lack of transparency around how AI actually works.”

These challenges are actively being addressed by researchers and developers, but they remain a key barrier to wider adoption.

Once solved, Glen believes AI will become a seamless part of both personal and professional life.

The Human Element

Despite his enthusiasm for technology, Glen repeatedly returned to one point.

Technology alone does not determine success.

Leadership does.

The organisations that succeed in the AI era will be those led by people who can:

AI may shape the tools businesses use, but human leadership will determine how those tools are applied.

It is this combination of technological capability and human insight that will ultimately define success in the AI-driven future.