​Listen: Airbnb user design experience manager Jenny Arden on design building trust, design-thinking and designer-founders

There’s no question design is having a moment. Fortune 500 companies are hiring chief design officers and investing in design and innovation centres, and even traditional corporates are getting in on the action. At the forefront of this is Silicon Valley-based Airbnb, the online marketplace for people to lease short-term accommodation. Founded by designers Joe Gebbia and Brian Chesky and co-founder Nathan Blecharczyk in 2008, the company is now a behemoth, valued at US$31 billion and located in 190 countries. On a recent trip to Auckland for the Better By Design CEO Summit, Airbnb’s Jenny Arden (an IDEO, Google and YouTube alumni) chats with us all things design. 

Have a listen to our interview with Arden, or have a read of the transcript below. 

Idealog: I’m here today with Jenny Arden, Airbnb’s user design experience manager. Hi Jenny.

Jenny: Hi there, nice to meet you.

So how are you doing today and how are you finding New Zealand?

It’s a beautiful day, bright blue skies, wonderful people – incredibly friendly and warm. It’s been a really wonderful trip so far.

That’s good to hear. So, I guess to start off with, would you be able to explain your role at Airbnb and how you’re overseeing hosts – or Airbnb customers – to become successful entrepreneurs?

So I run the design discipline of what I call ‘supply’. It’s the area of the business – thinking of Airbnb as a marketplace – there’s a customer that’s the guest, then on the supply side, that’s the host that actually puts their home on the platform. My role is to advocate for those people and they’re very, very different from our guest users. If you think about it, the typical guest user is opening up our app and booking a place maybe one or two times a year while they’re travelling. Our hosts are using our tools and hosting almost daily, so it’s a very, very different way of managing a team and thinking about the design challenges there. We also think of our hosts as micro-entrepreneurs, they’re actually running small businesses out of their homes, so we had to build tools for them that really work to fit in their daily lives.

In addition to focusing on what hosts are doing on a daily basis, my team focuses on some really interesting new challenges for the share economy – for example, policy and regulation. As cities enact different ways of making the share economy legal and fitting for what they need, economically, our team is producing tools in order for those municipalities to regulate. So for example, if you are allowed to host for 100 nights a year we have a nights counter to let you know how close you’re getting to that threshold. We also focus on other initiatives like anti-discrimination – making sure hosts do not deny a guest because of their race, their family status or their age. So it’s actually quite a large breadth of concepts and problems. It’s way more than just pixels on the screen.

So are you saying some people, as their full-time job, are hosts?

The way I look at is the moment you let a stranger into your home to sleep in your bed, you’re a host. At that moment, you’ve made that leap of faith. But there’s definitely a huge span of what it means to be a host. I’m staying at Airbnb right now, it’s a family that only rents out their home when they’re going on vacation, it happens a couple times a year, I happen to find at exactly the time I’ll be in New Zealand, and so they’re a very casual host. It’s definitely a family home, all their things are there and it feels very lived in. Versus our professional hosts – especially in our vacation rental markets – places that are destinations for travelers all over the world, those companies tend to have been around for decades and they’re definitely managing a large team, so they may have 30 or 40 people deployed helping welcome guests, making sure they have everything they need and really helping manage a company.

Obviously, trust is quite a key component between the host and the people staying there, so how do you manage that and what kind of role does design play in that?

Yeah, so design is at the centre of designing for trust, and that’s how we think about it at Airbnb – you’re designing for trust, meaning at all points in the process from the guest side and the host side, there’s a social contract that’s being created when you click that ‘book this listing’ button. At the end of the day, the mission of Airbnb is to provide belonging. All the language that we use, the screens that we design, we’re thinking about what does it mean to provide belonging and we believe by focusing on what does that mean and constantly iterating that over and over in these drops throughout the experience, you build trust.

I read a Fortune interview where Airbnb’s co-founder Joe Gebbia talks about ‘dog-fooding’, which was a new term for me, but it means using your own products to truly understand the user experience – so testing out the dog food, basically. Do you do this – do you test out Airbnb while on the go, and what kind of benefits does that add to the user experience?

I was first introduced to the term dog-fooding at previous companies. Google, in particular, is famous for this, especially internally. It’s part of their process and dog-fooding is basically what it sounds like – you eat your own dog food, so if you’re going to build it for users, before launching it to them and having them experience maybe your half-baked work, you should experience it for yourself and know what it’s actually like. So often dog food releases are released to employees only first so everyone in that company can realise what launching that product will do to the end experience. The real benefits of dog-fooding is first, obvious stuff – you catch all the bugs, anything that’s not working, you get it before it hits the customer. And secondly, you create a lot of empathy for the user, so you can actually really understand is this really changing everything for us, or do we add more friction? You start to understand the ramifications of the design decisions you made through dog-fooding.

In terms of yourself, your work identity and your role, do you think your more designer or entrepreneur?

I still feel I’m a hardcore entrepreneur and I use design to facilitate that. So for me, design is the best method for me in particular to express the intent of what the company should be doing. It’s a form of communication. But the reason why I pick entrepreneur is because a true entrepreneurial mindset is one that’s very scrappy, constantly changing, loves high-paced, high-stakes atmospheres, loves coming up with new ideas, incredibly innovative. All of these attributes I identify with, of course, I identify with the design community and love the trade of design, but I don’t get as jazzed up about the finite of the pixels and making everything perfect, the beauty of it, as much as what we’re trying to solve and how we’re going to change the world with it.

Airbnb’s office

I read that you have both a graphic design and physics degree, and you’ve also done a business programme at Harvard for creatives, so you’ve got a balancing act between the two. How would you describe that?

I do think pretty much all of my peers – all of those who are leading large design teams – have a left brain/right brain balance. It’s pretty rare these days to find someone who’s just into design, or just into the analytics. There’s so many multi-faceted leaders right now, that’s it kind of natural. User experience design is both an art and a science and I think you have to have both taste and subjectivity, and a way of describing things, those communication skills, in addition to analytical skills – you can talk the talk with the other peers you have. You have to be able to talk about data with your data scientist, your project manager, with all these other very analytical roles, and if you don’t have any of those muscles you’re not having a conversation anymore. So, it may seem like these two degrees are completely disparate and they are, but when you blend them together you actually have the skills needed to work with a multi-faceted team.

Yeah, and looking at the challenges the workforce is facing today, such as automation, it’s an unpredictable world out there. Do you think it’s important to bring both the design and business way of thinking to your work?

Yeah, and I keep saying this over and over but I really don’t see the difference anymore. When you’re designing a business, and I do mean you’re designing a business. There’s no longer ‘building’ businesses, you’re designing a business and what I mean by that is everything is completely intentional. You don’t accidentally build a company, you intentionally design a company. So the idea of design thinking merging with business, that’s what we’re doing. We’re figuring out intentionally, what is this company going to do, what does it look like and what are the players.

In our upcoming issue of Idealog, we’ve got an extract of Steve Vassallo’s The Art of Design. It talks a lot about how Silicon Valley is entering the age of the designer-founder, and companies like Airbnb are leading the way in this regard. What’s your take on this and do you think business is entering an era where design leads from the top down?

This is a hot topic right now – more and more designers are aspiring to be a founder. Almost every person on my team says that one day, they want to start their own company. These are all designers – 50 designers saying this. The reason is not only do they have someone to look up to, they’re starting to see designers have achieved this. What they’re also seeing is having the skill of storytelling and having the ability to get a group of people behind you is the superpower of a designer. A lot of these founders – Brian Chesky, CEO of Airbnb is famous for this – he is an amazing storyteller. He’s really, really clear on his vision, and that’s what makes him a great CEO as a designer. More and more people are starting to realise that if they can tell that story – tell what is really meaningful and purposeful – they can actually lead a company through that.

What are the challenges designers face when stepping into those executive or leadership roles?

A lot of it is execution-centric, so basic understanding of operations, finance, all the things that are involved when you create a company – you have to learn all of that as a designer. Very, very few designers have been classically trained, essentially, in business and they’re learning on the fly. Luckily, designers od have great intuition and most of the designers I’ve worked with have a humble sense, so they know what they don’t know. The CEO of Airbnb [Chesky] in particular, he is really great at understanding ‘I need people for this, I need to hire the right people to fill the void and gaps that I’m not filling. I can’t possibly do that job.’ And so I actually think it’s not necessarily the deficiency of the designer to fill all these roles, it’s up to that design founder to understand what they can’t do and get people to help them and hire the right people to fill those holes.

In your talk at the Better By Design CEO summit today, you said were a fan of the “dark horses and the misfits” in your hiring process. What do you mean by that and what kind of qualities do you look for in staff outside of just having design skills?

The dark horses and the misfits are those who have a bit of quirkiness to them. They’re not your mainstream tech-thinkers, there’s a lot of similar thought that goes on in tech in particular, meaning people read the same books, get inspiration from the same people and you start to see designs recycled and regurgitated throughout product. You see trends happening every year and there’s a tonne of companies that focus on trend reports because all designers are kind of following each other, they’re all looking at what’s on trend right now. What I look for are the designers who don’t pay attention to that as much, they’re inventing their own thing – they’re artists. They’re bringing inspiration from very rare sources you wouldn’t typically go for – they’re looking at photographers and writers and you know, physicists, other people for other sources of inspiration and creativity to really help them find solutions to the problems they’re faced with. If you have a really diverse set of brains, chances are you’re going to have a solution none of us individually would have thought of, but if you have a bunch of misfits and dark horses thinking about it, you have likely 60 different versions of a solution. Lets say you have a 60 person design team and half of them think the same, you’re going to have maybe 20 different solutions to the problem, so it’s all about diversity of thought and bringing in the people who have creative problem skills.

So you’re saying that plays into the whole diversity conversation as well? As I know you’re an advocate for more women in tech and design, so having those different thinkers and not just having a bubble of the same thoughts is really key.

A previous role that I held at IDEO, what was really interesting about that company when I was there is they intentionally recruited people who had really unique, non-traditional backgrounds. You could be on a team with an astronaut and they would call themselves a designer but they were an astronaut, because they wanted someone who would think like an astronaut on this project, or they would hire someone that used to own a vineyard, and that person would think like a horticulturalist as a designer. So, kind of strange, especially in tech, we have so many people who are lifelong technologists and know how Apple would do it and Google would do it, but when we look at really successful global teams with diversity, you want people who have a background that’s not the typical, and they would think about it in a really different way and create analogies from their past lives into the work that they’re doing right now.

The design disciplines – would you say they’re becoming really quite blurred?

Absolutely. Well, it’s two ways – blurred, but also more distinct at the same time. So people are definitely creating individual brands, like ‘I do branding’ or ‘I do product’. People are definitely going more in-depth in what they’re focusing on, but the blurriness is really is in not design disciplines, but cross-functional disciplines. So you have designers that are really fascinated with data and they’re data designers. Or I have designers who are impeccable visual designers and really want to do the marketing but they’re in product, and they’re the product marketers. So we have more people who are reaching across to other disciplines and merging them with design.

You’ve had an awesomely diversely career – working for Google as design lead on the self-driving car project, a UX lead for YouTube TV, an interaction designer and project leader at IDEO, and now the designer manager at Airbnb. What is the common thread connecting all these jobs?

With every single product and team that I join, the number one thing I look for is a mission – something that I can really connect to, something I actually care about. Because my job is to inspire a team and if I don’t care about it, I can’t do my job, so I always look for a product that’s on the edge of doing something really, really big and is solving a problem that I can actually identify with personally so I can get a team behind it, too.

Have you faced any gender-related challenges over your career and how have you overcome them?

During International Women’s Day, which is actually a new thing in the US, we don’t celebrate it like other countries. I heard in other countries you call your Mum, call your sister, post on Instagram – because of the whole #MeToo movement it became a holiday for us, we actually recognised it. During that day, there were a lot of conversations about what is it like to be a woman in tech and what are the challenges. Unconscious bias is real. It’s absolutely real. I was explaining to this group of women that day that every single performance review I’ve ever gotten for 16 years of my career, so my entire career, at least one person in my 360 feedback has said, ‘she’s a little headstrong’ or ‘she’s a little abrasive’ or ‘she’s a little bossy’ – all the words used for a strong female leader. It’s never the entire group of people I’m receiving feedback form in the performance review, it’s just one, or two, little tiny drops, little tiny bits in there, and you’re like, ‘Yup, there it is, I was waiting for it’. Just a word you’d never describe your male counterpart as. it’s never egregious or a huge glaring issue, but it’s the little drops that actually add up and count.

At your talk today, you were talking about how women are leaving the tech industry in rapid rates and you talked the fear of becoming obsolete and about making sure that if you’ve got a really great person employed and they go to leave for something to do with parenting, you keep in touch and maybe bring them back later down the line. Would you want to explain about that?

I’m a Mum. I have a two-and-a-half-year-old and a five-month-old, and I can completely relate to this heart-wrenching situation where we are the height of our careers, we’ve been working our tails off to get here and we want kids at the same time. It’s a really tough situation where we’re trying to have it all and you can’t. At some point, if you really, really want to stay at home and have that experience, you should be able to. But it shouldn’t mean you’re obsolete, and that’s actually the biggest fear of Mums, especially new Mums who need to take some time to raise children. They’re worried when they come back everything that they knew – the whole world they knew before – will no longer exist, and that they’ll have to start all over. I’m constantly reassuring people that there are some innate, baseline skills that you have, not just as a mother but as an employee with a certain amount of experience. The example I gave today, this woman is one of the best managers I’ve ever seen. Those are hardcore people skills. She knows how to grow talent, she has the ability. That is not something that’s ever going away in her life, it’s part of her. She’s a gracious host, she makes everyone want to work with her. These are qualities that will never go away and I have to reassure her that you need to sell yourself for those skills, not the ones you may not have, which will be the latest prototyping skills, or the latest trends in design, that stuff you can pick up in weeks. If you’re on it and okay treading water for a little bit, you can catch up very quickly. But the real core of who someone is as a person – those things never go away and I have to remind the people who exit not to forget that.

Another interesting point you said is it’s quite common in Silicon Valley companies now to have a lead designer that reports directly to the CEO, would you want to talk a bit about that?

Yeah, this is definitely a common trend right now. I’ve seen it be pretty much standard in the past six months and it started about a year ago to two years ago, where design leaders, especially as they’re joining smaller companies – companies that are about 100 people in size, say that they absolutely have to report directly to the CEO. The rationale behind that is that they want to create a balance in influence, meaning if you have a CTO, a CPO, all of these c-suite individuals, and you have one person that’s in charge of bringing up the user in all these conversations, you want them there when you’re making strategic decisions at the c-suite level. So if you’re talking about where you’re going to go in five years, what’s the direction of the entire company, you need to have someone that understands the user there to chime in and keep everyone in check.

Airbnb Open

To finish off, what’s the most valuable lesson you’ve learnt along the way in your career?

You know, I think that the most valuable thing is I’ve dealt with really, really small companies to really, really large companies, and the grass is never greener. You think you have it tough, and guess what – it’s hard. It is hard to build great product and you think that that company has it figured out, I’ll give you honesty here – Airbnb does not have it figured out. They’re still figuring out process, and how to grow people and how to recruit people. We do not have it all figured out. Google does not have it all figured out. We’re all still learning and developing and changing all the time, even though they’re making a tonne of money and loved by users all over the world, there’s always room for change and improvement. If you enter in with that mentality, you’re also always willing to flex and change and adapt and be a better leader. The most miserable people are usually those who have a fixed state of mind, especially in the tech world. If you think things will never change – that’s the moment you’re going to be really upset in your job, because by nature, by design, things have to change.

And finally, from being in the heart of tech and design at Airbnb, what are some of the key challenges designers are going to face in the future?

I think organisations are becoming more and more complex. Airbnb as it grows – we’re about 2000 people right now – as it gets bigger and bigger and bigger, it becomes more complex and more difficult to navigate. There’s a great case study that was written in the Harvard Business Review about the ‘Lego’ mentality. It’s this concept that when you’re a start-up and you have three people, you have a table covered in Lego and you get to build with all the Lego and all the Lego are yours, and as you hire more people you have to divvy up the pile of the Lego. So now you only get your little pile, but you get to build anything you want with that little pile. It gets wittled down and wittled down and wittled down as you hire more and more people, so the big challenge is not to think about ‘I have a smaller pile of Lego’ but to think about ‘What amazing thing can I do with that pile of Lego?’ So not look at your little world as being too small for you, but thinking about how can I absolutely transform this area I’m in charge of and make it really inspiring. Those are the challenges people are faced with right now as companies become bigger and bigger.

  • This piece was originally published on Idealog. 

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