An Interview with Chris Kalani, Co-Founder and CEO of Wake

After generating significant buzz during its six-month beta period, design sharing tool Wake launched to the greater design community earlier this month. Wake is leaner than other apps in its category — it’s designed to be transparent, enabling designers to share work effortlessly with their teams, and encouraging others throughout their organization to passively follow the design process. It also includes all the usual accoutrements a modern interface designer would want: mobile and desktop apps, Slack integration, and a Sketch plugin.

Wake’s intro video gained some notoriety within the design community when it was first released, due to its delightfully quirky (bizzare?) tone:

We spoke with Chris Kalani, the company’s co-founder and CEO, about the motivation behind Wake and its place in the design world.

Chris Kalani

Photo By Majd Taby (

What problem were you setting out to solve with Wake?

The biggest thing is to get designers’ ideas out into the open, sooner rather than later. Not just for the sake of the project or product that you’re working on, but also for the sake of the designer learning and thinking through things a bit more.

Facebook had a really cool culture which I’d never had at any other job. You had to answer for literally everything that you did. Pixelcloud, which is the tool that we used internally there, didn’t necessarily do that, but I wanted to create something that encouraged that sort of culture as well, so you’re not just creating things for the sake of it, but actually having to answer for why you’re doing it. If you’re continually sharing your process, you end up doing that implicitly over time because it’s all just laid out there for everyone to see.

Were you able to use Wake to design Wake?

Yeah, we were. When we started out, part of the team was in Oslo, and I was there off-and-on. Our lead engineer is in Germany, and it’s been super helpful for everyone to see what’s going on.

Tell us more about the Wake team.

We had an interesting start. We started in Oslo; my two cofounders run an agency called Bakken & Bæck out there. I think there are about 18 or 20 people there now. It started out as a project. I was out there, and we had a few ideas that we wanted to jam on together, and we built the first version of Wake with the team in Oslo.

Over the course of about six months or so we refined it, and decided, “Hey, this has some legs.” I had been thinking about the idea for a long time. So we turned it into an actual company, completely independent from Bakken & Bæck, and moved everything to the States.

There are three of us full-time here in San Francisco, and then we have our full-time engineer who’s been with it from the beginning — he’s in Germany. We have an iOS contractor who’s been with us for a while in Ukraine — he’s awesome. He’s a young, sharp kid. And then the relationship with Bakken & Bæck allows us to bring on front-end engineers, design help for marketing stuff here and there — we can scale up and down with resources there. For launch, for example, we got help from people. That’s on an as-needed basis.

How do you avoid feature creep and ensure you’re staying focused?

This is similar to a question I answered in the [Designer News] AMA. We defined the things that I think are important, holistically, like making sure that Wake is the fastest way to share and get things in front of your team. Having those guiding principles helped.

There are tons of feature requests and things that people ask for, but a lot of the time those things would get in the way of our core values, and so we either disregard them or spend a bit more time thinking about how we can achieve the request without compromising our goals.

For example, people like to organize things — they want to put things in boxes or folders, but I’ve been pretty bullish on not adding something like that for now, just because I don’t want you to have to think about organization or privacy or anything that would prevent you from sharing.

How has your experience at previous companies — Facebook, Jive, etc. — influenced your leadership style?

I feel like I’ve taken little things here and there from everywhere I’ve been.

Facebook, for example, gives you so much freedom. I didn’t go to school, so I’ve actually worked at a bunch of jobs, and everyone tells you, “As long as you’re doing your work, we’re cool with everything. You can come in whenever you want.” But it’s never true; nobody actually follows through with that. But Facebook is truly like that. If I wanted to come in at 1:00pm and work late, or leave early and work from home, or whatever — it honestly didn’t matter, as long as you were doing really great work and people could rely on you.

So I think that’s one thing that I’ve taken — just focusing on the work and the output of an individual, rather than focusing on the warm body in the seat at 9:00am. Holding people to really high standards and giving them a lot of freedom. That’s definitely something I’m trying to do now that we have employees. Giving freedom and letting people own their thing and trying not to dictate too much. That’s been one of my key takeaways.

How did you go about securing Wake’s initial customers?

A lot of them were from personal relationships. We sort of announced the product — just the basic concept — but never really told anyone what it was or how we were thinking about it, just to gauge interest. Dustin Senos was a buddy of mine who worked at Medium, and Katerina Batina is an ex-Facebook designer who went to Artsy, so we got them in.

A lot of people were either early Facebook people who I had worked with and had moved on, or other people that I’ve worked with over time. The first very small core were people that I had known or worked with before who were familiar with the problem, and then a lot of it was just feeding off that buzz.

We were in beta for six months or so, and over the course of that time we watched the queue of people signing up. We’d let people in that we thought were a good team and who’d hopefully be vocal about it, and so we kind of manufactured this buzz that was only coming from places like Airbnb and Medium, to make sure industry leaders were talking about the product.

What was the most valuable, or actionable, customer feedback you’ve had so far?

We don’t necessarily need a way to organize, but people want to be able to share a group of images as a single item. Wake is very one-dimensional in the sense that you can just share one thing, but it’s hard to tell a story. It’s hard to say, “Here’s the new signup flow. It starts here, then goes here and here.”

So I think that’s one of the things it’s lacking and that we need to do pretty soon. Better storytelling, and better ways to explain your thinking and pitch your idea.

How do you think Wake will influence the culture of organizations that use it?

I think there are a few pieces to it.

One, I hope that people who aren’t necessarily directly related to design or product development will have a better understanding of how their products or companies are being formed and thought about, and ultimately why certain decisions are being made. Facebook, with all the transparency that it had, and even with Pixelcloud — I’d still meet people that worked in different departments that didn’t even really know that we had a design team. They didn’t know how design worked. That was always shocking to me, because we’d spend so much time thinking about this and building the user-facing part of Facebook. I think if we can shed more light on that within other organizations, they’d be better off. And also potentially giving other people a voice to influence these things.

The second thing is giving designers an even louder voice than they currently have. If you get a good portion of a company on Wake, it could be a good way to get momentum around an idea, when before you’d have to get someone’s time in a meeting and pitch it. If you started sharing and circulating an idea, it could get some momentum that way.

The third thing would be helping designers think through their work and help each other become better and make more informed decisions.

What would you say is the biggest challenge facing the digital design industry today?

That’s a tough one.

Unrelated to Wake, I think a lot of it is just defining what our role is and how influential we can actually be within a company. It’s obviously getting a lot better, and we have more influence — we’re not just getting handed work and executing. That phase has passed, at least in tech. But I think a big problem with a lot of up-and-coming designers is that they’re still in the mindset of, “I make things look good,” focusing on executing instead of wrapping their heads around the big picture. Basically, I think designers need to realize the power that they have to influence things and sell ideas, and to have a massive influence on a company at the highest level.

You can find out more about Wake here, and sign up for the 30-day trial here.

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