Key to this job is conceiving and managing the execution of projects to engage the American public about Obama's policies - as well as presenting the US President in a favourable light, which Ashleigh says is often about presenting him as a human being with values, opinions, emotions and the ability to laugh at himself.
Projects lead by Ashleigh range from the simple-but-effective - such as showing the White House's support for gay marriage by lighting up the building with the rainbow flag - to providing visuals to support the President's yearly State of the Union address to Congress. This included 127 slides that also ran online alongside a live video feed of the speech, and which were designed to be shared on social media and so had to work without the context of the speech as well as within it.
Speaking at last week's D&AD Festival in London, Ashleigh revealed five tips for working on design projects that resonate with millions of people - and creating an effective team to achieve that.
"Engage people as people"
Obama's plan to make extensive changes to the US healthcare system required winning over the public, especially after the website to let people access the new healthcare schemes didn't perform well when it initially launched. Ashleigh noted that some within government suggested that the best way to introduce the change was with "a white paper or putting someone on a podium."
Instead Obama went on the Funny or Die's YouTube show Between Two Ferns with Zach Galifianakis (watch it below), a spoof interview show where the president was interviewed by a slovenly, aggressive and possibly drunk persona of Galifianakis' (who's best known for The Hangover movies). Here, between uncomfortable jokes, he managed to talk about the benefits of the new system, tell people the site was working fine now and even provide basic info about how to access it in to an audience that might not gain that information from news media.
"Encourage innovation"
"Even at the White House, a flat structure is necessary to give everyone a chance to thrive as a leader," says Ashleigh. Enabling people to lead their own projects encourages people to conceive and develop their own ideas, as they get to manage the creation of the projects they lead to (as long as they don't get too attached to them).
"Hire like you want innovation"
"Diversity breeds innovation," says Ashleigh - noting that there are two many different types of diversity including outlook, skillset and heritage. It's the last of these that gets the most discussion - and the creatives industries really do need to do more to hire more women and people from BAME backgrounds - but just as it can be unconsciously easier to hire people who look like you, you can also be drawn to candidates who think like you too.
This can lead to a kind of groupthink where everyone's getting input from the same sources (whether from their choice of media and experiences or the people around them), which can stymie innovation.
"We're the first administration to take interns from the opposing party," says Ashleigh. "We don't give them the keys to our social media accounts and let them post whatever they want," she laughs, but she says it's important that the staff represent all of the American people.
"Be authentic"
If you or your clients are too precious about your/their brands, you can lose the humanity that makes them appealing in the first place. Having fun with a brand can challenge preconceptions around it, and present a more 'true'-feeling image - even if the brand is engaged in a very serious business.
"If we can let the President and First Lady make fun of themselves, you can embrace that in your [or your clients'] business. It's about being authentic," says Ashleigh.
"Mistakes will happen"
Ashleigh says that there's nothing you can do to completely avoid mistakes, and says you shouldn't let the fear of them stop you from trying new things. Balancing taking risks with the ability to recognise quickly when something's working or not - and quickly adapting for that - lets you innovate quickly.
"Don't make fun of the President's ears"
"The worst thing you can do is make a joke about the President's ears," says Ashleigh. "Don't do it"