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Home FINTECH

Want to make your AI chatbot funny? Hiring comedians is a start

Siftedby Sifted
March 6, 2025
Reading Time: 4 mins read
in FINTECH, UK&IRELAND
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UK finance app Cleo may not be the best known AI chatbot on the market, but it has gained popularity among customers who enjoy its trademark mockery of their terrible spending choices. 

The finance-focused digital assistant will either highlight users’ good savings habits (“hype mode”) or point out all their bad financial decisions (“roast mode”). 

The roast option, which ranges from sarcastic to brutally honest, is the preferred setting for many of the app’s roughly 7m users. One off-hand barb reads: “Congrats you’ve saved £0! Double that and you could save £0 by next month!”

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If Cleo’s lines don’t read like the generic prose generated by other chatbots, that’s because 15 copywriters and content designers — some of them actual comedians — are writing these quips. 

London-based Ciara Jack is one of Cleo’s comedians, writing colourful jibes and put-downs for diligent money savers as well as the splurgers. “It’s easier and more fun to write roast mode,” she says.

Outside of Cleo, Jack has written standup shows and plays. She was headhunted by the fintech in 2021. “I thought it was a spam email at first,” she says. 

By and large, chatbots aren’t very fun conversationalists​​. They’re fence-sitters, unwilling to weigh in on sensitive topics, with most lacking the charm or spontaneity of real humans. “Some are in the ‘uncanny valley’ territory still,” says Jack. 

The art of writing an AI’s personality is to ditch the gratingly robotic stuff, she says, while taking care to avoid a dialect that’s overly niche. “We have to ask our American colleagues if there’s something an American audience wouldn’t appreciate or understand,” Jack says. “We don’t use ‘bin’ for example, so Cleo can’t say ‘get in the bin’. ‘Rather good’ — Americans wouldn’t say that either.”

A new career path

The behind-the-scenes character work on Cleo is a preview of the AI era where companies compete on who’s got the most human-like chatbot. 

Companies are usually bad at being funny, with some exceptions. For example, Duolingo, the language learning app, is not afraid to lean into offbeat humour. Duo, its owl mascot, is known online for being obsessively invested in users’ linguistic development, pursuing them night and day if they miss a Spanish lesson. 

Is it an inspiration when writing Cleo? “Duolingo is very cheeky but we can’t do that exactly. A huge component for us is empathy with the user,” Jack says. Knowing where to draw the line is important. “We cannot have Cleo say ‘How embarrassing’ if someone’s really low on money, for example. We have to make sure we don’t upset the user.”

It seems unlikely Cleo will enjoy a similar story arc to Duo. Duolingo recently killed off its breakout character, saying it had been hit by one of Elon Musk’s cybertrucks, only to resurrect the character some weeks later. “You can’t have Cleo get hit by a cybertruck,” says Jack. 

How to get a job like this

The tech world is ripe for comedians to poke fun at — but with all these chatbots arriving, the industry will have jobs to offer funny people too. 

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How do you get a job like Jack’s? Having a comedy background is obviously great but so is tech experience, she says. 

“I worked in publishing before. I wrote SEO-articles, meta descriptions so i was very tech literate, even though I hadn’t worked in a fintech. 

“It really helps to do a course on UX principles too,” Jack says. “Learn about user-journeys and how to create discovery. You also need to know how to write dialogue and learn to be concise.”

Usually for a comedian, the corporate job is the boring bit of your day; the evening gig is the fun thing. Jack says: “Being funny is a muscle so I’m happy I get to train it all day now.”

Read the orginal article: https://sifted.eu/articles/want-to-make-your-ai-chatbot-funny-hiring-comedians-is-a-start/

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