From Designer to CEO: An Interview with Wake Founder Chris Kalani

by Ruben Ruiz

posted on 03-22-2017

Most designers love what they do — and they’re great at it. So great, in fact, that their skills are in demand, not just for designing, but also as an integral part of the flourishing technology economy. There are plenty of examples of designers leading out in business. Founders of well-known companies, such as Airbnb and Kickstarter, were first designers.

Designers showcase a dynamic skillset and their creative minds are being recognized not just for artistic talent, but also for resourcefulness, ingenuity, and original thinking — core attributes of successful leaders. Great designers solve real problems. They translate business objectives into the products and features people want to use. It’s an elite group that can take a vision and make it tangible.

So, for designers who may be interested in pursuing entrepreneurial paths, what does it take to make the leap? We interviewed one designer-turned-CEO to find out — Chris Kalani, former Facebook product designer and now founder of Wake, an online collaboration tool for designers. He shares the top skills he learned as a designer and why they transfer so well to the world of entrepreneurship.

Be Open to New Ideas.

As a designer, keeping an open mind and looking for inspiration wherever you are is second nature. This skill of looking at something from multiple angles and coming up with a variety of strategies to solve a single problem will likely guide you to opportunities others haven’t seen or taken advantage of. According to Chris, “Wake kind of organically grew into a company. It started out as a project that just a couple of us were working on.” Once Chris knew he had something that designers wanted, he moved forward. He also had to be open to the idea of completely committing to this project. Chris says, “After about a year, we kind of got to a crossroad where we had to decide if we were going to go all in or not. ”

Tell a Story.

Designers have a knack for storytelling — after all, a picture is worth a thousand words. And a good logo tells a brand story. It’s this very skill that helps them sell ideas to people and communicate goals clearly. Chris’s ability to tell a cohesive story and then show it in a way that’s understandable is a skill he inherited from design and that still helps drive his business. Working with teams and being able to push ideas forward paves the way for organizing people around a common goal with a unified vision — vital for entrepreneurial success. Chris says, “As a designer, you learn a lot about storytelling. And the ability to sell ideas translates well into being able to sell your company and vision to other people. Whether that’s hiring or fundraising.”

Seek Out Inspiration.

One of the best design hacks is to seek inspiration from other great designers. Recognizing that you don’t know everything or have all the best ideas or answers on your own is key to success in every area of life. Chris relied on people in his network and friends of friends for understanding and inspiration. A lack of knowledge at the beginning of a new path is understandable, and searching for answers from the experts around you is a practical strategy for overcoming roadblocks and barriers to success. “In the early days I felt super helpless,” recalls Chris. “I had to surround myself with people who knew more and not be afraid to ask a ton of questions.”

Show. Don’t Tell.

Designers are fortunate to never need to rely on their words alone because they have the skills to create visuals, mockups, and prototypes. Building a business around a new idea can be tough and not everyone is going to see your vision for success. Chris convinced naysayers by literally going back to the drawing board. “Pixels talk. Mocks and prototypes speak much louder than words and can help you win or diffuse disagreements,” Chris advises. “Instead of arguing about my assumptions, I put in the extra time to show people what I believe to be right. When someone can see and feel a design or interaction you’re able to have a much more meaningful conversation.”


Designers work with a variety of clients, need approval from a team of stakeholders, and it takes a village to go from concept to final project. Chris believes the most influential designers are able to move ideas forward, and they do this through collaborative relationships. “It’s definitely important to build relationships with the engineers, product managers, and anyone else you’re going to be working with closely. It’s much easier to move ideas forward and get help when you have a good relationship with your team,” explains Chris. “Invest time in people because then they’ll invest their time in you and help you achieve whatever your goals are.”

With the innate ability to problem solve, influence decision makers, and collaborate with a variety of stakeholders, today’s designers offer high value with vastly marketable skills. Armed with expertise in a variety of design techniques, a keen understanding of the customer, and a great story, when you think it’s time to edge on up to the leadership table, it’s nice to know that you can depend on your creativity.

Topics: Creative Inspiration & Trends