In this episode of The AI Grapple, Kate vanderVoort sits down with Katelin O’Shea - Team Project Manager for the AI team at Dropbox Global Support, PRINCE2 Practitioner, and founder of AI That Works. With a background in operations and project delivery, Katelin brings a grounded, structured, and incredibly practical approach to AI that is accessible to absolutely everyone - no technical background required.
Her journey with AI began in 2021 with Copy.ai, using it to streamline complex grant applications. Since then, she’s exp...
In this episode of The AI Grapple, Kate vanderVoort sits down with Katelin O’Shea - Team Project Manager for the AI team at Dropbox Global Support, PRINCE2 Practitioner, and founder of AI That Works. With a background in operations and project delivery, Katelin brings a grounded, structured, and incredibly practical approach to AI that is accessible to absolutely everyone - no technical background required.
Her journey with AI began in 2021 with Copy.ai, using it to streamline complex grant applications. Since then, she’s experimented with everything from launching an AI-generated art store to building her own custom GPTs that automate the admin in her personal life. Along the way, she's developed a step-by-step AI implementation framework that's as effective for small businesses as it is for large enterprises.
What We Covered (and What You’ll Take Away):
💡 Start with the problem, not the tool
Katelin explains how shiny object syndrome can derail AI projects before they even begin. Her advice: identify the process first, then audit for opportunities.
⚙️ Her 4-question test to decide if AI is a fit
Ask yourself: Is the task repetitive? Time-consuming? Data-heavy? Frustrating? If yes, AI could help and you’ll be able to clearly measure the value.
📬 How she beat a parking ticket using ChatGPT
From voice-to-text storytelling to a legally formatted appeal letter, Katelin used AI as her legal assistant .... and won.
🧠 AI is 70% people, 30% tech
You can have the best tools in the world, but if your team doesn’t understand or trust them, it won’t stick. Katelin shares how she dedicates 30% of implementation time to building team confidence and tackling fears around job security.
📊 Messy data? Don’t let it stop you
Start with a small pilot and clean only the data you need. Katelin shares how large companies can avoid paralysis and how small businesses have an edge when building from scratch.
🗣️ Why AI transparency matters
Whether it’s an AI avatar or a chatbot, Katelin believes in being upfront with customers. Hiding it erodes trust - especially when AI inevitably makes a mistake.
🧠 Is AI changing how we speak?
From “navigating” to “demystifying,” Katelin questions whether AI-generated content is reshaping our language - and how that might influence communication more broadly.
📦 Custom GPTs that solve real problems
From her personal recipe and shopping list assistant “Susie” to writing legal letters for her mum, Katelin shares how small, tailored GPTs are her secret weapon for saving time and reducing friction.
🎨 Creativity without coding
With platforms like Replit, Cursor, and Lovable.dev, Katelin is excited about the ability to bring ideas to life without needing to be a developer. AI is lowering the barrier to innovation like never before.
🔮 What’s next in AI?
For Katelin, it’s all about accessibility, empowerment, and using AI to enhance - not replace - human creativity, strategy and connection.
🔗 Connect with Katelin on LinkedIn: linkedin.com/in/katelinoshea
🎙️ Listen now on your favourite podcast platform, and don’t forget to subscribe, rate, and share this episode with a friend or colleague who’s ready to make AI actually work for them.
