Rebekah Tolley: British Art Fair - Keeping Art Human Centric in the Digital Age

This is an episode about what art has always done in moments of technological upheaval: reflect them back to us. Rebekah Tolley curated British Art Fair's first digital art section in 2024, a show that broke records and helped formalize "Digitalism" as a recognized movement. She joins Christine to talk about AI-era artists as this century's surrealists, the echoes of the Industrial Revolution in today's anxieties about work and labor, and why human-centered art matters more, not less, as the tools get stranger — quantum-entangled sculptures, a shaman, and all.

About Rebekah Tolley
Rebekah Tolley is a hybrid artist, filmmaker, and arts educator with 25 years across fine art, photography, and digital media. She curated British Art Fair's first digital art section, helping launch Digitalism as a movement, and is now writing its first history, out next year.

Connect with Rebekah: LinkedIn | British Art Fair

About Christine Kahn

Christine Kahn is a Principal Technical Program Manager with 12+ years of experience across Playlist, Intuit, OpenTable, 20th Century Fox, and Realtor.com, specializing in AI/ML platforms and program delivery. She’s also a published musician and sound bath meditation practitioner. Dreams and Delivery is where she brings both worlds together — real stories from people who deliver at work and dream beyond it.

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© 2026 Dreams and Delivery LLC. All rights reserved.

This is a conversation about what it actually means to call yourself a builder in the age of AI agents, why judgment and taste turn out to be the scarce resource instead of production nowadays, and how the things you care about outside of work end up shaping what you choose to build.

At the moment in tech careers, tools are changing faster than job titles can keep up. Andrew Cunliffe has been living inside that moment for the better part of a year, building his own fleet of AI tools on nights and weekends while running design on Intuit’s AI+HI Expert Platform by day.

Andrew went from the 82nd Airborne to startup app development to 8 years at Intuit, where he now leads design for the AI expert platform inside QuickBooks and TurboTax. Outside of work, he’s built Raven MCP, an open-source design tool that runs a “taste engine” right inside your workflow instead of a separate canvas, plus HighLvl, a calorie-tracking app built for athletes.

Bonus: Andrew walks through a live demo of Raven MCP and explains why he made the deliberate choice to open-source it.

About Andrew Cunliffe

Andrew Cunliffe is a Senior Staff Product Designer at Intuit, leading design on the AI+HI Expert Platform inside QuickBooks and TurboTax. Outside of work, he builds and open-sources his own AI tools, including Raven MCP, a design system and “taste engine” for AI-assisted product work. Connect with him to see Raven MCP and his other projects in action.

About Christine Kahn

Christine Kahn is a Staff Technical Program Manager with 12+ years of experience across Intuit, OpenTable, 20th Century Fox, and Realtor.com, specializing in AI/ML platforms and program delivery. She’s also a published musician and sound bath meditation practitioner. Dreams and Delivery is where she brings both worlds together — real stories from people who deliver at work and dream beyond it.

Send us Fan Mail

Support the show

© 2026 Dreams and Delivery LLC. All rights reserved.

This is a conversation about what happens when AI screens resumes before a human ever sees them, why “AI integration specialist” means something different to everyone who says it, and the case for staying a generalist in a market that keeps chasing the next niche.

We also get into the quiet cost of the specialist bet, how fast a hot skill set can turn cold, and why the people who keep their base skills sharp are the ones still standing when the trend moves on.

Jack Smith started his career installing Windows 95 as a HelpDesk Tech and has spent the years since moving data centers, opening data centers, and learning over and over that the skills worth keeping aren’t the ones tied to a single tool or title.

Now, as AI reshapes hiring on both sides of the table, he’s watching the same mistake repeat itself: companies rolling three jobs into one impossible profile, and candidates rewriting themselves into keyword matches for roles they’ve never actually done.

Bonus: what 25 years of hard-won IT stories taught Jack about learning from failure instead of hiding it — the same instinct that led him to launch his own podcast.

About Jack Smith

Jack Smith is an Infrastructure Project Manager and the host of IT Horror Stories with Jack Smith, a podcast exploring the human side of technology. He spent more than two decades building a career across cybersecurity, data centers, networking, and digital transformation, learning that resilience comes from what you take from failure, not from avoiding it. Outside of infrastructure work, he’s been part of the demo scene — real-time digital computer art on old and new hardware — since 1991.

Connect with Jack: ithorrorstories.eu | LinkedIn | Spotify | Apple | YouTube

About your host
Christine Kahn is a Staff Technical Program Manager with 12+ years leading AI platforms and program delivery at Intuit, OpenTable, 20th Century Fox, and Realtor.com; and a musician and soundbath practitioner outside of it.

Connect with Christine: bio.site/dreamsanddelivery | LinkedIn

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© 2026 Dreams and Delivery LLC. All rights reserved.