The Agile Roundabout

The Data Roundabout: Experiences with Generative AI
📍 Hosted by Crosstide
🗓 Thursday 18th September
📍 66-67 Sun Ct, Cornhill, London EC3V 3NB
⏰ Doors from 6pm, Talks kick off at 6.30

Data Roundabout is our meetup for people working with data and AI – a space for practical inspiration, unvarnished lessons, and conversation that cuts through the hype. This edition: Generative AI in real life – where it’s working, where it’s not, and how to avoid the trap of using tomorrow’s tools to do yesterday’s work.

🎤 Talks on the night:

Steven Thompson
Technical Director @ Crosstide
"Vibe Coding: The Good, The Bad and The Ugly"
The way we build for the web has changed beyond recognition. Vibe coding promises speed and creativity, but it also magnifies risk. It can make great engineers fantastic, good engineers better, and poor engineers far worse. The real question is how leaders make sure it amplifies the right things.

Robert Hardman
Chief AI and Digital Transformation Officer @ Inchcape plc
"AI is about reimagining the future, not automating the past"
Paradigm shifts bring promise—and pitfalls. Robert shares real-world examples of what “new” means in business transformation, the traps companies fall into, and how to successfully bring GenAI into the C-suite without pouring money down the drain.

Sasha Bilton
CTO @ Planday
"Hidden Treasures: DIY GenAI to Clear Years of Backlog"
Meet Clarence, a Swedish VP of Sales who wiped out hundreds of low-value backlog stories and cut onboarding costs by 20%—armed with GenAI, a prompt, and a killer 80s soundtrack. Sasha will share how they did it safely, how it changed the relationship between sales and engineering, and how it’s sparked a culture of useful AI automation across Planday.

📍 Hosted by Legal & General
🗓 Thursday 9th October
📍 1 Coleman Street, London, EC2R 5AA
⏰ Doors from 6pm, Talks kick off at 6:30pm

Agile Roundabout is our community for product thinkers, delivery leaders and transformation specialists – a space for honest lessons, shared experiments and conversations that reflect the real complexity of scaling teams.

This edition explores how organisations are making the shift from output-driven delivery to product-led, value stream-aligned ways of working – with real-world stories of what’s working, what’s hard, and how to make it stick.

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### 🎤 Talks on the night:

Ben Smith
Product Director @ AutoTrader
“Autotrader Product & Technology – The Eras Tour”
From humble beginnings to a constantly evolving operating model, Ben will take us on a whistle-stop tour of the eras of Product & Technology at AutoTrader. This talk will explore:

• How Autotrader’s team structures have evolved over the last decade
• The principles that have shaped their transformation
• Key challenges they’ve faced and how their model has adapted
• Their new ‘Community Era’ and what it means for scale and culture
• Reflections on leading and organising tech communities through change

Expect honesty, insight, and some Taylor Swift-level reinvention.

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Olya Kosousova
Head of Delivery @ Times Media, News UK
“From Silos to Flow: Restructuring Teams to Accelerate Value”
News UK recently restructured its delivery model around outcome-led “North Stars”. Olya will cover how they:

• Designed and iterate cross-functional teams
• Developed T-shaped skills and collective ownership
• Identified the right metrics to drive delivery
• Removed blockers to unlock speed

A real-world look at how to turn vision into velocity.

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Victoria Leslie-Kent
Transformation Director @ Lloyds Banking Group
Talk title TBC
Victoria brings deep experience leading transformation at scale. Full details coming soon — but expect an enterprise view on embedding product models in complex organisations.