The Intelligent Enterprise

For many enterprises, the first thing they do with a powerful new technology is use it to do the same work for less. Matt Harris thinks that’s a missed opportunity. As co-founder of Darkstar Development, Matt works with CEOs, CFOs, and boards at the point where AI ambition meets operational reality, and he can usually tell within minutes whether a company is headed toward growth or just a cheaper version of what it already does. 

In this episode, Matt joins host Tom Stoneman to talk about why data strategy has to come before implementation, how he makes the case to a skeptical CFO, and what separates organizations that are set up for the long term from those that pay for shortcuts later. He shares two real examples: a company that built its data foundation first, and a startup that moved fast and skipped security. We also hear how Matt resets in a late-’90s Nissan Skyline, and the question he wishes more executives would ask. 

Follow The Intelligent Enterprise for new episodes every two weeks on Spotify, Apple Podcasts, YouTube, or wherever you get your podcasts. 

What does it mean to own your work when AI helped you do it? In part two of our conversation with Ryan Bascos, Renad Morrar, and Ritu Bhalodia, the discussion moves from first encounters to everyday reality: the pressure to use AI faster and more often, the question of whether the skills they trained for still matter, and how each of them sees AI impacting their career future. 

We also find out how this generation actually switches off, and the answers are more honest, and more complicated, than you might assume. 

Follow The Intelligent Enterprise for new episodes every two weeks on Spotify, Apple Podcasts, YouTube, or wherever you get your podcasts. 

This is Part 2 of a two-part conversation.  

Most of what we hear about AI in the enterprise comes from the top down. But someone has to go back to their desk and figure out what it all means. Ryan Bascos, Renad Morrar, and Ritu Bhalodia are in their mid-twenties, early in their careers at Digitate, and part of the generation that was handed AI just as they were figuring out how to work. 

In part one of our interview with them, we hear about what it actually feels like to integrate these tools as they start their careers, how AI impacts their feelings about the future, and what growing up alongside something really does and doesn't teach you about it. Host Tom Stoneman and producer Grace Heerman join the conversation too, and discover that every generation has had its version of this experience. What's different this time might just be the speed.

Follow The Intelligent Enterprise for new episodes every two weeks on Spotify, Apple Podcasts, YouTube, or wherever you get your podcasts.

This is Part 1 of a two-part conversation. 

We're taking a short break from new episodes while we plan some exciting upcoming interviews. In the meantime, we're revisiting one of our favorites from the archive on a topic that's even more relevant now than it was when we released it in 2025.

As enterprises move from AI pilots to full deployment, the upskilling question has gone from 'nice to have' to urgent. In this episode, Tom Stoneman sits down with Ricardo Costa, Chief Technology Officer at Purolator, to explore the big idea of preparing the workforce for AI.

With nearly two decades leading technology and security teams, Ricardo has helped organizations through multiple waves of change. Now, his focus is on giving people the skills and confidence to use AI well. Tom and Ricardo dig into the gap between AI expectations and reality, why upskilling can’t be a side project, and how strong teams and partnerships make change possible.

We also hear how Ricardo uses music and specifically makes AI-generated music as his own “outside the enterprise” ritual to reset and find headspace for better decisions.

Follow The Intelligent Enterprise for new episodes every two weeks and stream on Spotify, Apple Podcasts, YouTube, or wherever you get your podcasts.

For Ugo Orsi, the era of command and control management is over. AI doesn't just change what gets done. It changes who decides, who leads, and what that leadership means. 

In Part 2 of this conversation on The Intelligent Enterprise, Ugo moves from the ethical framework he laid out in Part 1 to what it actually looks like on the ground. The executives who will navigate the AI transition well, he argues, are the ones willing to become coaches rather than controllers. The ones willing to be challenged by their own teams.  

Ugo draws on two real-world examples – companies that used AI to free up significant portions of their workforce and chose not to use that as an excuse to cut headcount. The through-line in both cases is clear values. He also has a clear answer for the question a lot of leaders are sitting with: should we pause AI deployment until we figure this out?

As enterprises move deeper into AI adoption, the question is no longer just about what the technology can do, but about who is responsible for what it does.  

In Part 1 of this two-part conversation, host Tom Stoneman sits down with Ugo Orsi, Chief Customer Officer at Digitate, to discuss why AI ethics are less abstract than they sound. Tom and Ugo discuss AI’s ability to improve society, manipulate behavior, disrupt work, and weaken critical thinking when people begin using it as a substitute for judgment. They also explore why AI has no humanity of its own, and why human leadership is more important than ever as we decide where the technology should and should not lead. 

Beyond the immediate risks of AI adoption, this is a conversation about what happens when speed becomes the most valuable measure of intelligence. This is Part 1 of a two-part conversation. 

AI agents are incredibly powerful tools, but how can we be sure they’re actually generating value? As enterprises move from experimentation into production, the harder question is no longer what AI can do, but whether AI can efficiently deliver useful results without burning through the budget.

In Part 2 of this conversation on The Intelligent Enterprise, host Tom Stoneman continues his discussion with Ash Ashutosh, CEO of Pinecone and a three-time founder, to explore how agents may soon become the new users of enterprise systems. Ash explains why Pinecone built Knowledge Query Language, a system not designed for humans, but for agents that need a native language of their own to retrieve knowledge quickly, accurately, and within real-world business constraints. 

Beyond the technical breakthroughs, Ash looks at the organizational shifts AI is forcing into view, and why the enterprises that learn to manage cost, accuracy, and true human creativity together will be best positioned for what comes next.

This is Part 2 of Tom’s two-part conversation with Ash.

When it comes to effectively rolling out AI in companies, middle managers may be more important than ever as the link between strategy and daily work.

In Part 2 of this conversation on The Intelligent Enterprise, host Tom Stoneman continues his conversation with Melissa M. Reeve, author of Hyperadaptive: Rewiring to Become an AI-Native Organization, to dig into the practical side of how businesses can become AI-native. Melissa argues that AI should be treated less like a software rollout and more like the arrival of the personal computer in the 1990s: an industry-redefining shift that requires infrastructure, training, and new ways of working.

Their discussion also turns to the human side of AI transformation, detailing how AI can interfere with an individual’s professional identity, why leaders need to protect the psychology of their teams through that disruption, and how Melissa protects her own time by keeping AI off the kayak, out of nature, and away from family time. 

This is Part 2 of Tom’s two-part conversation with Melissa.

If your enterprise is failing at AI, it isn’t because you picked the wrong tools. You're failing because you're trying to layer AI on top of legacy systems without changing anything underneath. 

In this episode of The Intelligent Enterprise, host Tom Stoneman sits down with Melissa M. Reeve, author of Hyperadaptive: Rewiring to Become an AI-Native Organization, to dig into why so many AI investments still fall flat and what it actually takes to fix that. Melissa draws on decades of research into how enterprises evolve to make the case that the path forward isn't faster adoption, it's deliberate transformation. 

Together, Tom and Melissa unpack why functional silos made sense in a post-war economy but become a liability in an AI-driven one, how friction and fidelity loss quietly kill good ideas on their way up the chain of command, and what separates an organization built to optimize from one built to adapt. 

This is Part 1 of a two-part conversation. Part 2 drops in two weeks. 

Ash Ashutosh has spent nearly thirty years building technology that disappears – the kind that works so well, nobody has to think about it. That obsession with invisible infrastructure is what drew him to Pinecone, and it's shaping how he thinks about the next chapter of AI. 

In this episode of The Intelligent Enterprise, host Tom Stoneman sits down with Ash, CEO of Pinecone and a three-time founder, to explore what it means to build for a world where AI agents, not humans, are increasingly the ones doing the prompting. Ash explains why that shift required a rethinking of the whole stack. He also shares how Pinecone put that thinking into practice internally, scrapping dashboards in favor of a system that both surfaces data, and tells you what to do with it. 

Beyond the product, this is a conversation about what it means to stay relevant across multiple technology waves, and why the people who treat their hard-won experience as a foundation rather than a finish line tend to be the ones who end up ahead.