How did you get into content design?
Creating for audiences
Before Cleo, I worked for more than a decade as an actor and comedian. As I worked more consistently, my goals started shifting: I no longer wanted to just be an actor. I wanted to be a financially stable actor with health insurance. Uh oh!
As you may have heard, acting doesn’t pay well. [Insert rant about the US arts suffering due to policy issues here].
Waiting tables wasn't exactly my childhood dream, so after the years, the lack of fulfillment coupled with significant financial challenges eventually meant it was time for a Big F*cking Change™️
Recovering arts major
Let’s talk about the challenges of a limited resume. Not to be dramatic, but I couldn’t even get a job answering phones (your loss, giant real estate agency who shall not be named!)
So when the 2019 COVID closures hit, my career exploration switched into high gear.
I had two goals:
- Find a stable career path that's not only affordable but fulfilling
- Figure out how to leverage my existing skills as invaluable assets
Enter UX bootcamp — I fell in love with design thinking, product vision, and unyielding consideration for the audience aka the user. In a few months, I had a (much-less-expensive-than-law-school) UX / UI design certification, and a chance to build cutting-edge products with real, measurable impact.
I really didn’t make the connection early in my post-bootcamp job search that I might be the right fit for UX writing or content design. That quickly changed when I found an entry-level UX writing opportunity at Cleo — the listing asked something like, Do you know comedy? Scriptwriting? UX design processes?
Many frantic "yes's” later, here we are.
What does your week at Cleo work like?
My experience at Cleo is a bit different than most who work on the app. I’m based in the US (hello from Chicago 👋 ) but my two cross-functional squads are based in the UK.
To outsmart time zone differences, my early week involves “async” communication through reading updates instead of attending morning meetings.
Midweek is great for head-down focus time. If you guessed that’s writing, you’re partially right.
- Observing user research
- Collaborating with engineers
- Looking at how parts of the app are performing
It depends on the stage of the project and what the goals are.
The end of the week means content update summaries. Over-communication sounds like a bad thing, but when you’re 100% remote it can be a lifesaver.
On Fridays, we wear pink. No. We usually have a virtual squad hangout with games (cause we’re grown-ups at work) or a retro where we look back at the two week’s work.
Content designers belong to a chapter called "Swearswords." The name comes from a very public spelling mistake made by a previous writer (um, legend) 💅 ✨
We're a team of six responsible for creating and managing app content. Our weekly sessions involve collaborative writing in a shared Google doc, often backed by the Barbie movie soundtrack.
We also help make Cleo the smartest chatbot in the world. That means assessing and refining Cleo’s AI-generated chat responses. The AI is excellent at contextualization and recognizing patterns, but our human touch is what preserves Cleo's distinctive voice and assures the LLM (Large Language Model) is trained on only ideal inputs.
What do you like most about working at Cleo?
I love the problems I get to solve and the people. So much.
How has AI affected your current projects and processes?
It’s been wildly impactful. Both in my role as a content creator and in developing Cleo as an app. It’s shifted how we find content solutions to user problems and, personally, it’s reshaping how I write content in my day-to-day.
That means educating myself on AI is key — which is a challenge because it’s almost like a moving target, the landscape changes so fast. To keep up, our content design team sets aside dedicated time for sharing insights and educating each other. Recently Cleo employees were granted access to a new continued education platform and I'm excited to use it to keep exploring AI resources.
So I feel super lucky to be at Cleo right now because of all the hands-on exposure to AI and real-time learning.
What are some challenges you face?
Balancing usefulness, clarity, and Cleo’s humor is always a necessary challenge. Sometimes you come up with an absolutely fire gag, but you always have to consider: “Is this the right message for this user at this point in the journey? Does this add value to the experience? Is this joke accessible?” You have to be willing to kill your darlings.
Where can we find you when you're not working?
Forever trying to find the best gluten-free ramen on earth.
At home reading to my cat (we love Dorothy Parker).
Doing something physical because I have too much energy.
Any advice for copywriters facing a competitive marketplace that is obsessed with AI?
Short answer: Stalk industry thought leaders’ socials and start Googling terms and concepts.
Long answer: I think many of us are initially drawn to writing for the instinctual elements. Wrangling generative AI comes less naturally. So, do two things: learn about AI (which anyone can do) and keep telling compelling stories (which no one can do like you, especially not generative AI).
If you understand the functionality and limitations, you’ll learn where your beautiful, funny humanity fits in.
Interested in joining us?