Gladys: The ChatBot That Won an Innovation Award (& Why That Matters)

If you'd told me 18 months ago that an AI chatbot named Gladys would win an Innovation Award for Gladstone, I’d have laughed. 

Not because I didn’t believe in AI, but because I knew how these awards typically worked. The recipe for success? Launch a new product, showcase its revenue stream, and deliver a polished corporate presentation.

But this year, we flipped the script. And we won.

The Moment Gladys Took the Stage

The Jonas Annual Business Awards (JABA) is a serious event. Sixteen businesses from across Jonas Europe come together to celebrate success, share best practices, and let’s be honest, size up the competition across the portfolio. Gladstone had entered the Innovation Award before, always making it to runner-up but never quite clinching the win.

So, what changed?

First, our CEO threw out the corporate playbook and went full stand-up comedian. Instead of the usual “here’s our new product, here’s how much ARR it generates,” he delivered a comedy monologue (yes, really). Picture this: a slide deck not filled with product screenshots, but a dancing AI cat. The audience laughed—and if you’ve ever seen a room full of executives, developers, and salespeople, you’ll know that’s not a common reaction from one half of the room! Developers were intrigued, executives were mildly alarmed, and sales folks? Well, they were fully on board the second they realised it would save them admin time.

Second, our innovation wasn’t about a new revenue stream—it was about efficiency and operational effectiveness, which ultimately benefits our customers. Gladys isn’t a product we sell; she’s an internal AI assistant, helping us work smarter so we can focus on delivering better solutions. That’s what made our entry stand out.

Who (or What) is Gladys?

Gladys is our AI chatbot, but she’s not just any AI chatbot. Unlike generic ChatGPT, she’s been trained to understand our business, our industry, and even our tone of voice. She speaks British English (because re-proofing all those Z’s to S’s is soul-destroying, not to mention my personal hatred of the overuse of emojis targeting Gen Z'ers). Plus, she answers even the daftest of sales queries with the nuance of someone who’s worked in Product Management for years.

She started as an experiment. Back when Word first started correcting teh to the (which, honestly, felt like magic at the time), I was already fascinated by how technology could make life easier. So when ChatGPT arrived, I thought, why not? I jumped in, testing how far I could push it beyond its default, often painfully dull “might as well write it yourself” responses.

Some content marketers dismissed AI as “cheating.” But why would you choose to dig your vegetable plot by hand when you could use a shovel for the heavy lifting? AI isn’t here to replace creativity, it’s here to help us move faster, think bigger, and refine our ideas. The real skill isn’t just having a ChatGPT login; it’s knowing how to craft its output into something meaningful.

But the real magic happened when we combined the art of prompt engineering with real technical expertise. While I was crafting Gladys’ personality, our CTO, Mark, was building a private, gated AI bot, let’s call him Carlos. Carlos was brilliant at understanding our product data but… let’s just say he wasn’t the world’s best communicator.

At one point, he mysteriously started responding in Spanish, which considering Mark was watching Love Island while building it—might explain a lot. And so, naturally, the sales team started calling him Carlos, and enthusiasm quickly faded. Perhaps it was the Love Island influence, or maybe Carlos just had a certain flair for DuoLingo. Either way, for a brief period, our AI-powered sales assistant was inexplicably bilingual.

Eventually, we merged the best of both worlds: Gladys’ human-like responses + Carlos’ deep product knowledge and Gladys 2.0 was born. And it worked.

So, Why Did We Win?

Honestly? I still don’t know exactly what convinced the judges. Maybe it was the humour. Maybe it was the AI cat. Maybe it was the fact that Gladys represents something every business in the Jonas portfolio can learn from - AI isn’t just about new products; it’s about embracing automation and transforming how we work.

What’s Next?

Winning this award was a proud moment for me and Team Gladstone. More importantly, it proved that AI isn’t something to let pass you by. Anyone can use it, and when used well, it allows you to focus on the things that truly make an impact - whether that’s improving customer experience, strengthening your brand, or simply standing out from the crowd. And, as we found out, it can be a lot of fun along the way.

I'll be sharing practical prompt engineering tips, whether you're a seasoned marketer or just curious about using ChatGPT to improve your content. No PhD required, just simple, effective ways to get better results from a marketing chatbot.

From building Gladys, I’ve learned what works, what doesn’t, and how you can apply it, whether you're creating content for your club, crafting the perfect holiday itinerary, or, let’s face it, looking for that extra edge when contesting a parking ticket!

Stay tuned. And if you've ever had an AI bot suddenly start speaking an unexpected language, let me know apparently, it happens!

Top tip: maybe it's got something to do with what you’ve been watching on TV...