One company now has more AI agents deployed in its organization than it has human employees. Slack's CMO Ryan Gavin dropped that stat into a conversation with Craig Smith, and then immediately identified the secondary problem it creates: when your digital workforce outnumbers your human one, how do employees know which agent to call for which task? That orchestration problem, and the conversational interface that solves it, is what this episode is really about. Gavin describes Slack bot's transformation from a notification tool into what he calls the ChatGPT moment for the enterprise, an AI that doesn't just understand the internet, but understands your business, your team, your customers, and your company's entire conversational history, all the way back to day one.

The conversation covers the full arc of what this shift means in practice: a Salesforce executive walking into an unfamiliar meeting and being praised for their questions, because Slack bot had prepared them in minutes using the team's full history; a marketer who built his own data scientist agent over a weekend and is now completely unshackled from the bottleneck that was slowing him down; and Gavin's most honest admission, that he's been saying for years that AI won't replace jobs, but this is the first time he actually believes it, because the soul-crushing "work of work" is finally shrinking, and what's left is the kind of creative, high-energy output that people actually want to do. The inbox, he says, is a deathtrap in the AI era. The companies that figure out how to move beyond it will outperform their competitors by multiples.

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Zendesk went private two weeks before ChatGPT launched, and the moment it came out, it was obvious that customer service would never be the same again. Shashi Upadhyay, head of product, engineering, and AI at Zendesk, joins Craig Smith to explain what the company has built since: a self-improving AI system that doesn't just resolve tickets but learns from every failure, studies what the human did to fix it, and gets measurably better over time. He calls it the resolution learning loop, and for Zendesk's best customers, it's already resolving 70 to 90% of incoming tickets autonomously, up from the 10 to 20% that chatbots managed just a few years ago.

The conversation goes deep on the engineering decisions that actually matter: why hallucination is a feature, not a bug, and why the real challenge is knowing exactly when to switch from creative AI to deterministic code; why Zendesk acquired Forethought and what made their approach to going live in days rather than months so valuable; and why, despite all the momentum, Upadhyay estimates we are only about 5% through the adoption of AI in customer service. The bottleneck isn't the technology, it's the change management required to restructure how human and AI workforces operate together. His vision of the end state is striking: personal AI agents talking directly to enterprise AI agents, resolving 90% of issues instantly, while humans focus exclusively on the complex, high-value interactions that genuinely require them.

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AI agents can now connect to every tool your employees use. The problem is that connecting them and trusting them are two completely different things, and most enterprises have figured out the first without solving the second. Oren Michaels, co-founder and CEO of Barndoor AI, joins Craig Smith to explain why that gap is the defining challenge of the agentic enterprise era. His framework is simple and sharp: agents are like enthusiastic interns. They will absolutely do something when you ask them to. Whether it's what you intended is another matter, and when an agent can act across Salesforce, Slack, email, and calendar simultaneously, the blast radius of a misunderstood instruction is far larger than anything a human intern could cause.

The conversation covers the 100,000 agent problem - the reality that each agent handling a discrete task needs its own set of rules about what it's allowed to do, and that number scales to a size no human team can govern manually - and why traditional identity management systems were never built for the failure modes AI agents create. The new threat isn't bad actors getting in; it's authorized people using allowed tools with agents that still do the wrong thing. Barn Door's governance layer sits between the agent and the tools it can access, specifying exactly what each agent is permitted to do in each context, and Venn brings that same capability to individuals who want to understand what's possible before their organizations catch up. This is one of the most practically useful conversations available about what enterprise AI governance actually looks like.

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Every time you hit a phone tree or a chatbot with canned answers, you're experiencing the gap between what AI can already do and what most companies are still delivering. Craig Smith sits down with Tom Chen, Chief Product Officer at Aircall, to explore why that gap is closing fast, and what it means for any business that relies on voice as a customer communication channel. Tom makes a case that is both practical and counterintuitive: AI voice agents aren't better than your best human rep, but they are better than your average one. They never get frustrated. Their patience is infinite. Their tone never changes. And they can handle 100 concurrent calls at a fraction of the cost of a human operation, without lunch breaks, without bad days, and without going off script.

The conversation covers a finding that should change how any business thinks about AI adoption: when one of Aircall's customers gave callers the explicit choice between a human agent and a faster AI agent, far more people chose the AI than anyone expected, and satisfaction scores went up. Tom also identifies the real bottleneck that most businesses don't see coming: it's not the AI technology, which is increasingly commoditized. It's the tribal knowledge, the undocumented expertise that lives in the heads of long-tenured employees and never gets captured anywhere, that determines whether an AI agent performs well or not. Until that knowledge is surfaced, even the best voice agent will underperform.

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Most AI systems follow a gradient, a mathematical slope that tells them exactly how to improve, step by step, toward a known goal. Neuroevolution doesn't follow any gradient. Instead, it runs hundreds or thousands of competing solutions simultaneously, spreads them across the space of possibilities as broadly as possible, and lets the best ones recombine, the same logic that drives biological evolution. The result, as Risto Miikkulainen explains to Craig Smith, is creativity: solutions that no human designer would have anticipated, that emerge routinely from the evolutionary process.

Miikkulainen is a professor at UT Austin and VP of AI Research at Cognizant AI Labs, and he has been working on this field since the 1980s, which makes him both a historian of it and one of its most active frontiersmen.

The conversation covers a remarkable range: a mystery model that outperformed every competitor in a recent stock trading competition with forensic footprints pointing to neuroevolutionary AI; Sakana AI's system that autonomously designed experiments, wrote a paper, and had it accepted at a major machine learning conference; and a pandemic decision system that trained overnight and made country-specific recommendations by morning, with Iceland actually following some of them, all the way to the prime minister.

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One in four people over 65 will experience a fall, and for most of them, the technology designed to help is a device that hasn't meaningfully changed since the 1980s. Chia-Lin Simmons, CEO of LogicMark, joined Craig Smith to make the case that this gap is both unnecessary and solvable, and that AI is finally making it possible to shift personal safety from reactive to predictive. Her company's Freedom Alert Max doesn't just detect falls after they happen, it builds a personalized digital twin of each user, tracking steps, sleep patterns, and medication adherence over time to identify the subtle signs of health decline that even daily caregivers often miss.

The conversation is one of the most grounded and human discussions of applied AI you'll hear, covering why Apple Watch fall detection was engineered for crash detection, not elderly falls; why AI can flag a problem but a human needs to hear the breathing on the other end of the line; and why the 700,000 caregiver shortage in America makes technology like this not a luxury but a scaling mechanism. For anyone navigating aging parents, their own future, or the sandwich generation pressures in between, this episode is both practically useful and genuinely moving.

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Luiz Domingos has spent 25 years watching enterprise communications evolve, from IP telephony to cloud to AI, and his assessment of where things stand now is unusually concrete. Companies have moved past the strategy deck phase. AI is being embedded directly into contact centers, compliance workflows, and communication pipelines, and the question executives are asking has shifted from "which model is smartest" to "which deployment reduces friction and stays compliant." Domingos is direct about what gets in the way: you cannot pour AI into a legacy architecture and expect transformation, and cloud-only AI doesn't solve the latency or data sovereignty problems that regulated industries face every day.

In this conversation with Craig Smith, Domingos covers the practical mechanics of how Mitel is applying AI across its portfolio, from real-time transcription and sentiment analytics in contact centers, to agentic workflows that turn conversations into automated tickets and follow-ups. He draws a clear line between AI agents (which give recommendations) and agentic AI (which takes actions), a distinction the market consistently confuses. He also makes a prediction worth noting: within five years, voice will replace the traditional app interface as the primary way people interact with enterprise AI systems. For any CIO or CTO trying to move from experimentation to real ROI, his framework - start with workflow friction, not pilots - is the most actionable takeaway in the episode.

A fly with 100,000 neurons can fly, find food, and reproduce. A $100 million supercomputer cannot. Dr. Terry Sejnowski used that observation to silence a room full of MIT AI researchers in the 1980s, and it remains just as sharp today. Sejnowski is one of the foundational figures in the history of deep learning, co-inventor of the Boltzmann machine, and a professor at the Salk Institute who has spent his career studying both the brain and the machines we build to imitate it. In this conversation with Craig Smith, he turns that dual perspective on ChatGPT, and what he finds is something genuinely clarifying: not a human mind, not a threat to humanity, but an alien intelligence that has absorbed more knowledge than any brain ever could while remaining fundamentally empty when nobody is talking to it.

The conversation covers the full landscape of what current AI is missing - from goals and reinforcement learning to the constant self-generated flow of thought that defines consciousness - and why the word "understanding" is so ambiguous that even the world's top cognitive scientists can't agree on whether ChatGPT has it. Sejnowski also makes the case that hallucinations aren't a flaw to be engineered away but the flip side of creativity itself, that we are in a pre-Copernican era when it comes to understanding intelligence, and that the real future of AI lies not in scaling language models further but in looking at what nature has already solved, from field mice to fruit flies. His new book is written for the general public and available now.

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