Life at Cleo

Cleo's Biggest Marketing Experiment

Cleo just wrapped our first out-of-home multi-faceted marketing campaign, Money Main Character. It was a massive effort, involving multiple moving pieces that took place within a span of just two months. How did we accomplish this? Here’s a timeline and thoughts from our team

HOW CLEO PULLED OFF OUR BIGGEST MARKETING EXPERIMENT: Money Main Character, featuring our first-ever Chief Spending Officer


In August 2023, Cleo’s Marketing department set out to brainstorm the company’s fall campaign. The brief given to the team was: do something big.

Allison O'Conor, Brand Copywriter on Hype Squad, recalls that “NPCs (non-playable characters, for those not familiar)” were a mainstay in the pop culture lexicon around this time:

“I think we were just spit-balling in this meeting and I was like, ‘what if we had somebody spending money, and Cleo users can vote how they spend it?’ Then it just built from there with all the different prongs. The team had also seen viral job listings that made us laugh, like how that hotel was hiring a Ken to do ‘Beach’... So this campaign really was born from current pop culture trends and just asking the question, “what can we do that’s big and weird?”

Eventually, following those initial brainstorms, Allison proposed our campaign, Money Main Character. Her idea posed the question: who is better at giving financial advice, humans or AI? One lucky human would be chosen as the test subject to have their spending decided by Cleo users, against their will. The decision would be based upon a daily audience vote in our app, and this Money Main Character would have to spend their money accordingly. Cleo would give this person an allowance of $545 a week, an amount based on research around the estimated average disposable income of a young adult in the United States. 

Once Allison got buy-in from key leadership on the idea, things got real. Cleo would hire a Chief Spending Officer, who would become the Money Main Character in and out of the app. The position would be a month-long contract with $10,000 in compensation on top of the weekly spending allowance, and we would aim to create a viral moment by hiring our CSO via TikTok. At first, Money Main Character was conceptualized as only a week-long engagement with daily voting, but we later decided to extend the contract time of the position for a month with once-weekly content following the main campaign.


To actualize this larger-than-life idea, we agreed that Money Main Character needed real-life activations beyond acquiring our Chief Spending Officer. This campaign was our first time using both guerilla strategies to raise brand awareness. Externally, we teamed up with our PR agency O’Hear & Co., and creative marketing agency Flight Story.  

Internally, we sought support from several squads. We worked with our “Spend Better” product squad led by Group Product Manager Matt Alcock, who helped build out the in-app experience. We also worked closely with our CRM department to coordinate support on email marketing. When it came time to hire our Chief Spending Officer, we needed to ensure all legal terms were sound with our Compliance department and worked with our People team to publish the job listing. 

September was spent ideating and planning each moving part of the campaign. We discussed the voting mechanic in-app and what our audience would be deciding each day, in-person activations, influencer contracting, and advertisements. Flight Story was largely supportive in crafting the campaign narrative and ad deliverables with our team. We planned to have a billboard and posters strewn throughout Williamsburg, Brooklyn- the latter would be swapped out each day to match the daily voting prompts our users would receive. Our team made the choice to have the wild posters include local businesses where possible in the copy to make the advertisements feel more personal. We also decided to incorporate a street team element where people on the street would be handed free Cleo tote bags and QR codes to download our app. 

Our PR agency, O’Hear & Co., would assist with signal-boosting our Chief Spending Officer position by coordinating distribution across outlets and job sites such as Monster, LinkedIn, and Indeed. PR would also have a huge lift post-campaign, pitching our Money Main Character’s detailed experience as a diary, documenting their journey. Our influencer team contracted five macro-influencers to support the campaign on TikTok by duetting our application once it went live. 

After the exact details of the campaign were finalized, we needed to hire our Chief Spending Officer. 


Our Content Producer Emily Winberry posted our job application via Cleo’s TikTok on September 26th. The instructions were simple: duet our video and answer the questions listed to be considered for the position. Lastly, the hashtag #CleoCSO had to be in the applicant’s caption. We used the hashtag to measure awareness, which garnered a million views. The only requirements for the position were basically:

  • Be 18 years of age or older
  • Have experience with content creation and a willingness to document the journey

We closed applications on October 3rd and took our time carefully narrowing down our candidates. One video stood out above the one thousand duets that came pouring in, and that was Rana Ahmed. Though we received dozens of great submissions, she felt like the perfect fit for the role. Once the ink dried on Rana’s contract, we onboarded our new CSO and got to work on firming up plans throughout October for the big week of our campaign at the end of the month.

We flew Emily out from Los Angeles to Brooklyn so that she could be with the team in person for the week at a co-working space we booked in Williamsburg, Brooklyn. Amber Jones, Project Manager of Flight Story, also joined us in person to manage our street team and their shifts throughout the week.


On Monday, October 30th, daily Money Main Character in-app voting commenced at 9:00 am EST. The campaign wild posters began appearing in Williamsburg, Brooklyn that same day, while our billboard went up Tuesday the 31st on 1st and Kent. Amber was proud that the team was able to pull off this massive effort for the campaign:

“New York City has a lot of status as a global cultural and economic hub, so the most rewarding part of this campaign was helping Cleo enhance their brand recognition in one of the most vibrant cities in the United States. Executing a high-visibility billboard concept in Brooklyn was a great way to maximize the reach of the Chief Spending Officer campaign, and the exposure Cleo now has to locals and tourists alike is something to be proud of. The biggest 'wow' moment for me was taking over the Williamsburg area with our big billboard by Domino Park, paired with our wild posters in hotspots around the area – seeing everyone's hard work come to life was really cool, and I feel honored to be a part of something so unique.”

Users were notified by Cleo each day to pick between two options for Rana’s spending in the app. Votes closed around 3:00 pm and were tallied by 4:00 pm. Once the results arrived, our team immediately briefed Rana on how to film her vlog that evening. After our Money Main Character completed the following day’s video, it was delivered to Emily later that evening for editing and final touches. The vlog and results would then be shared each morning via TikTok after keeping our audience in suspense overnight. Since the content involved hours of editing, Emily had a large lift during what was the most active part of our campaign, but she found enjoyment in seeing the results play out:

“It was just so fun to do something like live and you know, [that’s] actually responding to what people were voting on. I thought [that] week was so fun, even though it was a lot of work. It was great to see people vote and then respond with a video that they voted on. It was a fun way to interact with our followers.”

We repeated this process daily until Friday, November 2nd, then weekly through the remainder of the month.


Before the 30th, we had Rana film some of her content ahead of the campaign so that we could have as much content as possible rolling out in real time between vlogs. Each morning, we posted a video where Rana shared that day’s prompt, reminding users to go vote in the app. Different prompts presented unique challenges for their respective videos. When users voted for Rana to go get a $100 spa treatment, our team had to find a day spa that was still open on Monday in Brooklyn after 4:00 pm where Rana could pay for a service plus tip. When the votes skewed towards the more expensive spends, we assumed users would lean towards the splurges we created. We were wrong.

The next day, our audience told Rana they wanted to see her DIY costume skills on Halloween. Rana and our team ventured to the nearest Spirit Halloween, thinking there would be some good deals with Halloween ending hours later. What ended up happening was a spontaneous burrito costume made of tinfoil, which resulted in Rana getting a free meal at Chipotle for ordering a meal dressed up. Our Wednesday prompt asked our audience to pick between an expensive Michelin-star meal or drinks at a dive bar, and when Cleo users voted for the latter, we realized Rana doesn’t drink. Instead, we got creative by sending Rana to a non-alcoholic craft beer bar, Talea Tap House. 

This trend continued with Thursday’s vote, when people made Rana take a $5 Citi Bike ride in the cold with free leftovers as a post-workout meal, instead of attending a spin class in a warm studio followed by an acai bowl. Realizing $5 on a Citi Bike didn’t get you much time yielded some funny results. The final day of daily voting was anti-climactic as well; users voted for Rana to stay home instead of going out and blowing her budget. As the rest of the month continued, our audience told our Money Main Character that they wanted her to continue to save, which involved cooking and meal-prepping. 

At the end of the day, should we be shocked that Cleo users chose the smart option? The answer is, no. We learned that our audience has been inspired by their favorite AI financial assistant to make smart choices, and this was certainly a reminder for Rana as well, as she shared in one of her vlogs: 

“I’m honestly really surprised because I thought everyone had the same spending habits that I did, but it’s really making me check myself and notice how much I spend.”

For Allison, seeing everything come to life made it worth it: 

“There was a real element of like immediate execution, the fact that we had the people on the street, that we had real signs, that we had this real person connecting with the app and like showing people how the in-app experience works- even though it wasn't like necessarily the same as the way the consumer uses the app- it affected her day to day life. I thought that bridge was interesting.”


When asked what was the most challenging part of the campaign, Amber said “Executing a guerrilla campaign is no small feat, and in these cases, you always have to expect the unexpected. With a wild poster concept, you don't have a clear idea on how long your advertisements may stay active – I may see our posters in a high-traffic area at 9 am, but if I walked by an hour later I may see that the posters were covered up by another brand or torn down by the construction workers handling the scaffolding. It was important to set the expectations that the nature of this sort of campaign is truly ‘wild’ in nature, and we had to remain agile in our approach and rely on the other elements in the campaign as a whole to push the message and make a meaningful impact. Thankfully, we activated in over 25 areas in Brooklyn, so if one set of posters came down we knew there were plenty more that lasted, which kept things really interesting each day.”

Emily felt that she learned the importance of staying organized, saying ‘having all the content planned out beforehand was super helpful. I definitely learned that doing so much work ahead of time really helps. The week of, I felt pretty prepared- I knew how each video would go depending on what was voted on. We learned to adapt as the week went by, like with the [QR code] handout, I think it’s important to allow yourself to change and grow during the week of the campaign instead of getting frazzled and not panicking and being like, ‘oh well, we didn't do that, oh no’- being able to think on your feet is like a great skill to have in that setting.”

Most of all, communication was crucial, and our team felt that was the most crucial challenge of all, as explained by Allison: 

“This was my first time spearheading something of this size. I tried to make sure everybody was in the loop about everything and double, triple-checking that everybody's told everybody else their ‘stuff’. It was way more than we've done in a campaign before- the fact that it had the hiring element, soliciting responses on social media and we were trying to make that a PR story- that was just the beginning; that in itself was low-key almost as big as some of our past social-led campaigns. So I would say just like the length of time and then like the multi-pronged, as we say, approach to it.”


What does the next big Cleo campaign look like after Money Main Character? How will it be similar? Allison shared what she thought that could be: 

“We're increasing the scale and scope of what we can do, and the fact that we can work with external partners is so helpful. I think having a face to the campaign was amazing, so carrying that element over would be interesting. That just helps humanize what's going on. Whatever we do next, I think the goal should be to keep going bigger and getting weirder.”

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