Cathal O'Shea

Blog

Thoughts on AI, technology and building products.

Career Product

100 days at Stripe

Oct 20, 2026 · 5 min read

Reflections on my first 100 days in Product Strategy & Operations: setting the pace, building context, writing as a craft and working with AI.

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A stone landing in a jade lake, with ripples spreading across the surface

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AI Product

Notes on Customer Service AI Agents

Jun 30, 2026 · 17 min read

A working tour of AI customer service agents: what separates an agent from a chatbot, why support is an early proving ground, and how players like Fin, Decagon and Sierra are scaling.

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Community Events

A Year of Hackathons

Dec 30, 2025 · 6 min read

A first timer's retrospective — lessons on shipping fast, meeting builders and how these events have become more accessible.

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AI Commerce

Building Trust in Agentic Commerce

Oct 6, 2025 · 7 min read

AI agents are moving to the core of digital commerce. This post explores what agentic commerce is, why it's accelerating now, and why building a trust layer is essential for secure autonomous transactions.

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AI

How Popular Is GenAI?

Sep 30, 2024 · 4 min read

From overflowing AI workshops at the AWS Summit to global survey data, this post examines who is actually using generative AI and how awareness and adoption varies across age groups.

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AI Product

How GenAI Will Empower a New Era of Product Builders

Apr 18, 2024 · 5 min read

Generative AI is democratizing product development. Learn how these tools are leveling the playing field for builders and what you can do to stay ahead of the curve.

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Events

Reflections on the Silicon Valley MBA World Summit

Jan 2, 2024 · 3 min read

A look back at the Silicon Valley MBA World Summit: key lessons from sessions on technology and entrepreneurship, plus thoughts on the power of ideas and connections.

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