The AI Grapple

In this episode of The AI Grapple, Kate vanderVoort, Founder and CEO of the AI Success Lab, sits down with Chris Nolte, Founder and CEO of Kayana Remote Professionals, to unpack what’s really happening at the intersection of AI, remote work, and human capability. Chris brings the rare lens of an investor-operator who has led and scaled businesses across finance, retail, prop tech, healthcare, and real estate. As an early beta tester of OpenAI and a long-time advocate for global talent, he shares grounded insights into why AI adoption often stalls, and what leaders are getting wrong about jobs, productivity, and automation. This is a practical, human-centred conversation about execution, not hype. Meet Chris Nolte Chris Nolte is the Founder and CEO of Kayana Remote Professionals, a company helping growth-minded businesses, nonprofits, solopreneurs, and PE and VC-backed portfolio companies scale using top-tier Filipino talent, supported by AI-enabled matching and workflow automation. Before Kayana, Chris spent 17 years running a family office where he bought, built, and operated companies with long-term capital. He has served as President and CEO of Verlo Mattress, co-founded AneVista Group, and advised startups through Dragonfly Group. His work today sits squarely at the intersection of AI, remote talent, and the future of work. Why AI Tools Don’t Automatically Change How Work Gets Done One of the central themes of this conversation is what Chris calls the human execution gap. Many organisations invest heavily in AI tools, only to find that very little actually changes. Chris explains why this happens and why the real barrier isn’t technology, but the expectation of full automation without redesigning roles, workflows, or accountability. Kate and Chris explore why AI still needs human judgment, why unfinished automations are everywhere, and why execution breaks down when leaders expect tools to replace thinking. AI, Repeatable Work, and the Future of Remote Roles As AI takes on more repeatable, task-based work, the nature of many roles is shifting fast. Chris shares why this shift doesn’t spell the end of remote work, but rather raises expectations for what remote professionals contribute. Entry-level, low-context roles are disappearing, while higher-level work is becoming accessible far earlier in a career. The conversation reframes the fear around AI and jobs, focusing instead on how remote workforces can move up the value chain rather than being pushed out. Global Talent, AI, and the Levelling of Opportunity A powerful thread in this episode is how AI is reshaping global opportunity. Chris explains why AI is acting as a great enabler for talented people in countries that historically lacked access to education, capital, or global markets. With AI closing gaps in language, research, and communication, opportunity is becoming more evenly distributed, even if outcomes are not. Kate and Chris discuss what this means for competition, wages, and the reality that professionals are no longer competing locally, but globally. What Makes Remote Professionals Irreplaceable With AI available to everyone, differentiation now comes from distinctly human qualities. Chris outlines why professionalism, discernment, curiosity, and output-focused thinking matter more than ever. He explains why remote professionals must actively learn how to operate at a professional standard, and why trust is built through consistency, judgment, and ownership, not just technical skill. Kate adds real-world examples from her own team, showing how AI-supported workflows free leaders from bottlenecks while raising quality and expectations. AI, Custom GPTs, and Scaling Expertise The episode dives into how custom GPTs and AI workflows are changing knowledge transfer inside businesses. Kate shares how embedding her expertise into AI systems allows her remote team to work in her voice and style, reducing rework and approvals. Chris builds on this by explaining how content, education, and even books are changing as AI becomes part of how people learn and apply information. This section offers a glimpse into how expertise can now scale without burning out the expert. Productivity, Pace, and the Reality of Change AI is moving faster than people can adapt, and both Kate and Chris acknowledge the tension this creates. They discuss why productivity gains don’t come from layering AI on top of broken processes, and why many organisations are stuck between fear, regulation, and falling behind. The conversation also touches on global differences in AI adoption and the long arc of change businesses need to prepare for. Looking Ahead: The Future of Work That Never Sleeps To close, Chris shares his view on what’s coming next. He describes a future where even small and mid-sized businesses operate across time zones, supported by AI and distributed teams that follow the sun. Work doesn’t stop, even when leaders do. The result is faster execution, higher output, and more opportunity for people who know how to work with AI rather than around it. Key Takeaways AI adoption fails when leaders expect automation without changing how work is designed Repeatable, low-context roles are fading, while higher-value work is becoming accessible earlier Remote professionals compete on a global stage, with AI as the common denominator Human judgment, curiosity, and professionalism matter more, not less AI scales expertise best when paired with strong workflows and clear standards Connect with Chris Learn more about Chris’s work and Kayana Remote Professionals: Kayana Website: https://www.hirekayana.com Kayana Capital Website: https://kayanacapital.com/ LinkedIn: https://www.linkedin.com/in/chrisnolte/