Ready to Sharpen Your Creative Chops? A Q&A With Upwork’s Creative Director

Ready to hone your skills as a creative freelancer but not sure where to start? Jonathan Cofer leads Upwork’s creative team, overseeing a huge scope that includes brand development, Upwork’s visitor website, events like the Work Without Limits™ Executive Summit, videos, and even Upwork swag.

The path that brought him to Upwork includes a period as an independent contractor; he understands what a challenge it can be to polish your skills when you don’t have the constant feedback you might get in-house. In this Q&A, he shares his experience and some of his top tips to learn more and expand your skillset.

Q: How did you get to Upwork?

Jonathan Cofer leads Upwork’s creative team
I’ve always been into creative activities, such as drawing and photography, and I’ve also been a bit of a computer nerd. So I wanted to do something creative with computers, and that took me to the Academy of Art in San Francisco. I studied Computer Arts, a program that basically teaches you a bit about everything: photography, video, audio production, graphic design, coding, product design. It gave me exposure to a lot of different areas, something that’s been very handy as a creative director working across so many different creative disciplines.

After graduation, I started as a freelancer. This really taught me about the business world and working with clients—the business side of design. From there, I worked with an agency called Lunar, primarily doing product design with the occasional branding project.

I moved to Elance (now Upwork) because it was an interesting opportunity that seemed a particularly good fit with my freelance experience. I started just days after Elance and oDesk merged and I was drawn to the challenge.

Fast-forward to today: I oversaw the rebranding from Elance-oDesk to Upwork in 2015, which was a huge undertaking, and have built out our design team from almost nothing. When I started, I had one in-house designer that reported to me. Now I have a hybrid team with ten in-house designers, copywriters, project managers, and a bench of ten freelancers in five different countries that I can turn to, depending on the project.

Q: What are some of the core skills you learned by running your own business?

A: Learning to work with clients was huge: I learned how to communicate better, present ideas more effectively, create project schedules, and set expectations. I also had to create my own budgets and manage my time and resources.

I went to Lunar because I’d never worked at an agency. I found I was well prepared for the things I needed to do, and I think I grew more quickly within the agency because of my freelance experience.

Q: What advice would you give to self-employed designers who want to level up their skills?

A: It is tougher to make sure you’re learning and growing when you’re on your own. I think pursuing a range of projects and clients helps: a lot of leveling up just comes from time and experience.

If you follow design blogs and get involved in the design community, you can kind of recreate the culture that you’d get at an agency: stay on top of trends, look for inspiration, have conversations. The more you can network online the better.

And try new things with clients. Try to push the boundaries. It can be intimidating but remember that many clients want you to push back; they’re paying you because you’re an expert and they want you to tell them if something isn’t a good idea. Not all clients want this, however! You need to learn to adapt your strategy.

Q: What should a designer consider before starting their own business?

A: Early on, I thought I couldn’t start a project if I didn’t have all the answers. The thing is that many clients don’t know what they don’t know. Now I have a completely different approach: have a conversation, ask questions, ask followup questions.

As the expert, it’s your job to ask for the information you need. And sometimes, clients don’t have the answers. Really wear the customer service hat and focus on helping clients in every way you can. Help them fill in the gaps. Design freelancers who can do this well are the ones who succeed.

Q: What sets top-notch freelance designers apart?

A: Beyond talent, I really want to work with people who are proactive. For example:

  • If you don’t hear from the client, you reach out and ask
  • You don’t wait for a client to tell you to do something if you think you can go ahead and do it to make things more efficient
  • You’re overly communicative and you’re usually very quick to respond

It’s really about what a designer does to take care of the client relationship. I think great creatives are always on top of their projects and aren’t afraid to push back or ask followup questions. When a designer does their homework, it makes the client’s life much easier.

Q: What will matter for designers in 5 to 10 years?

A: If I look back at the skills I was taught in college…it’s hard to predict the future! Staying up-to-speed on the latest trends will indicate the skills you need.

I never would have anticipated the Apple Watch or the iPhone when I was learning to design. Now we have AR (augmented reality) and voice control. Design will always change and evolve. As these new formats come out, learn about them, see how other people approach them, and adapt your own skills.

Some skills will always be important: How do you talk to people? How do you explain your design so clients see the value? When you think about the longer term, don’t forget these essentials.

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