Derek Briggs 

Zauber Brewing — Derek Briggs is a Designer at Red Guava, which is the team behind Cliniko, a healthcare practice management system used by thousands around the world. He previously worked at Neo and Fine Citizens. He’s a lover of pixels, code, and beer. Preferably all at once.

First things first, tell me a bit about your early life as a motocross racer. I heard that you had quite the career.

When I was three and a half I was given my first motorcycle from my dad. He was big into motocross before I came along and wanted to pass that skill and experience to me. I raced for that whole next summer and then started kindergarten. I raced every weekend and actually learned how to ride a motorcycle before I learned how to ride a bike. My show and tell item at school was always the trophy I won the week before. I raced competitively on a circuit for the next twelve years. It was a very non-traditional childhood, but it’s always a good story.

Derek Briggs
Derek Briggs is a Designer at Red Guava.

I didn’t realize that motocross competitions for kids would be so demanding of your time.

Oh, absolutely. It felt like I spent more time traveling than going to school. When I turned sixteen years old I had the opportunity to go pro, but at that point I was tired of racing. I had done it for twelve years and never had much of a social life.

So you were burned out?

I really was. I raced for so long without having the option of stopping. I wanted to hangout with my friends instead of just racing all the time, so I took a few years off and got into cars. When I was nineteen I bought a street bike, and I started doing stunting on that. It was just so dangerous and there were so many crashes.

I would think!

It got out of hand and I lost a few friends to it. When I was twenty I became a father and that was it. It would have been selfish of me to risk my life, so I sold the bike and just quit. There are videos out there of me doing different stunts. When I watch them I can’t believe that I didn’t get more hurt.

One of the last big crashes that I had I wasn’t wearing a helmet, which was stupid of me. I was doing an endo, which is when you ride on your front wheel. I clipped a road reflector and it kicked the handlebars back and forth and flipped me off. I slammed into the ground and sliced my head open and that led to three layers of stitches.

Every once in a while I’ll hop on a bike, but I just can’t control myself and end up doing a wheelie or an endo. It’s still fun to me, but I can’t touch them so that I don’t get hurt.

But you look good! I wouldn’t have thought that you had such a bad crash.

My stepdad is a physician, so I called him and asked, “Hey should I go to the ER? Or should I just come to your office? I’m going to need some stitches.” He stitched up my leg and face and to this day my forehead on the left side is pretty numb. Most of the nerve endings have been sliced in there. That was my last big crash and the moment when I realized that I had to stop.

So being a designer is a safer vocation?

Yeah, a little bit [laughing].

How did you get into designing for the web?

A friend of mine, who did video production work, was using Photoshop to design street bike posters. I was just amazed at how he was able to manipulate the photos and at how powerful Photoshop was, so I started playing with it too. That is what got me started.

I then went to Ohio State for CS, but it didn’t last long enough. The curriculum was outdated and I just wasn’t having it. School just wasn’t for me, especially after growing up and doing motocross. I did the bare minimum of what I had to do and that was it. Learning on my own allowed me to grow at a much faster pace. I was able to stay on top of the most up-to-date technologies and not have to learn about how we used to do it.

I started my first design gig at a screen printing place in Lima, Ohio, which is where I’m from. I also went back to school at American Intercontinental University Online for visual communications. I lasted about a year there and again, it just wasn’t progressing fast enough for me.

Coding and design is just a hobby. I just happen to get paid for it.

A good friend of mine, and fellow designer, got me an opportunity to do an apprenticeship at a hospital in Lima, which was key to getting me where I am today. I told them, “I want to learn and you don’t even need to pay me. I’ll even work forty hour work weeks.” I moved back in with my parents and worked for free. They liked what I was doing and after a few months asked me to stay on full time.

Fine Citizens

Later on I realized that being in Lima wasn’t going to provide me with the opportunities I needed to further my career. So I pursued some leads and moved to Columbus to work for Fine Citizens. After a couple years of just doing interface design, I jumped into HTML and CSS and initially it was really intimidating.

What pushed me to learn it was my frustration with the developers who coded my designs. The comps that I would create wouldn’t be translated one-to-one into code. There’s really no excuse for that with the tools we have and the capabilities of the browsers we develop for. I understand that older browsers are limiting, but with newer ones, the design on the page should look nearly identical to the comp. I decided that I had to do the work myself to ensure that it’s done to my expectations.

You’re the best judge of how the designs should be developed.

Yeah and it’s so much faster than sitting with a developer and insisting that something be changed so many times over. “Change this, change that, change that…,” it just makes more sense for me to do it myself.

I’ve now found that I spend much less time prototyping a design because I switch to code so much more quickly. I know the direction that I’m going towards and start building.

So designers should learn to code?

Absolutely. I didn’t realize how important it was initially. When I worked at Fine Citizens, I went the entire job not doing any coding and I know that our developer was so frustrated with how nitpicky I was about my designs. Designers should do it themselves, so it’s easier for everyone. Designers need to fully understand and embrace the medium that they are designing for. It will only make them a better designer.


When I worked at Neo my development skills really took off because of the brilliant people I was working with. I got to sit in a room full of developers, so I learned development. It’s career-changing, especially when you can build for the medium that you’re designing to. It makes your designs so much easier to translate to code because you know what’s possible and what’s not. I one hundred percent think that all designers should learn how to code HTML, CSS, and JavaScript. They’re only going to do themselves a favor by doing so.

With every engineer that I work with I tell them, “Don’t bother to style anything. Get your part of the code working and then send it back to me.” That’s all I want. It’s so much easier for them because they often don’t want to do it, while I do. Each of us doing what we’re good at.

Designers need to fully understand and embrace the medium that they are designing for.

What’s your workflow like?

I try to get into the code as fast as possible. I use Sketch because a year and a half ago a couple buddies were like, “Dude, you gotta try out Sketch. It’s super awesome.” It took me about a week to get used to it and then I ditched Photoshop.

No turning back?

No turning back! Sketch takes away so much of the fluff that’s in Photoshop that you can’t even do on the web. Everything that you can do in Sketch can be done in CSS, which makes it super convenient to design with. I design the general layout and direction that I want to go in and then start coding. It’s such a waste of time to polish the design on canvas because there’s going to be constraints in the browser that you don’t expect.

How do you feel about being a generalist versus being a specialist?

I am a generalist because I don’t want to restrict myself from learning new things. Nobody in this industry should restrict themselves to only doing one specific thing well. Sure there are specialists who are really good at what they do, but you can’t stop the motivation to learn more.

Being a generalist also makes you much more marketable as an employee. I’m fortunate enough that I can do the jobs of two people, so you don’t have to employ a developer and a designer.

What is Red Guava and what do you do there?


It’s a great story of how Red Guava came to be. Joel founded Red Guava as a consulting firm to help fund the development of Cliniko, which is the practice management software that we build and maintain. Joel’s wife is an osteopath and the software she had available to her was terrible. He quit his job to focus on building the product as an alternative solution to the terrible software solutions that were currently available. He was a .NET developer who wanted to learn Ruby and he used Cliniko as a way to do that.

Joel assumed that Red Guava was going to need to do consulting work too, but Cliniko just took off. We recently hit 3,000 customers and we’re incredibly proud of that. The company is solely owned by Joel, which is awesome because we don’t need to deal with any pressure from investors. Joel knows what he wants and he’s driving the company to success.

Would you speak about your transition to working remotely at Red Guava?

I thought it was going to be really hard to leave an office, but it’s been easier than I thought it would be. You can really buckle down and be motivated by yourself.

At Red Guava we have no structured meetings whatsoever. We meet up whenever we have people online, but there’s so much autonomy that if you think that something should be done, you just do it. Joel is very passionate about that. He hires the best people for the job and trusts us to do what’s best for the company. Everyone we work with is just brilliant at what they do.

Working remotely helps me get started right after I wake up. I don’t have to worry about the commute to work. I can grab my computer and start working within a matter of minutes, which really helps with my productivity. So many studies have shown that people are more productive in the morning. I’ve thought lately that a lot of companies could benefit by having their employees come in at lunch, so that they can crank away as soon as they wake up.

I usually have my lunch around 11:30 AM, so after that I take a shower, get dressed, and I’m totally refreshed. I’ve already got a lot of stuff done, but now I’m ready to resume working. It’s such an awesome workflow and I didn’t think that it was going to work out that well for me.

One thing I miss is the commute home, when I would unwind in the car. There would be days when I wouldn’t even turn on the radio, but reflect on what I got done that day and whether it was the right solution.

There’s another Red Guava developer in Columbus, John, and we alternate working at each other’s homes one day a week. It’s nice to be able to work together like that. Jason, who designs at GitHub, lives down the street from me, so I’ll crash at his house some days too. It’s nice to get out of the house because otherwise I wouldn’t ever leave.

I make it a point to talk with my coworkers through video chat, so that we get that face-to-face interaction. Obviously, it’s difficult because we live so far away, but I want to learn about them as people. Everyone thus far has been extremely awesome and personable. I just got back from Australia a couple weeks ago and got to meet everyone there. It was an experience to meet these people who I only knew through text. I want to know them outside of work too.

Any designer who wants to learn to code needs to join a consulting firm, specifically Neo if they’re in Columbus, because you’ll work on something different everyday.

What are the differences between working for a consulting company versus a product company?

It’s a complete one hundred and eighty degree change. Consulting was a lot of fun, and any designer who wants to learn to code needs to join a consulting firm, specifically Neo if they’re in Columbus, because you’ll work on something different everyday. It played a vital role in where I am today.

Consulting is difficult because you’re doing work for someone who’s paying you, so they want to control the development decisions. We did have some clients who fully trusted us and they were a lot of fun to work with, but then you have those clients who are really stubborn, and they want to make the decisions even when we’ve told them that something is a bad idea.

Working for a product is different because we make the decisions for ourselves, so we can do what we think best. Everyone at our company is personally invested in our product and focused on making it the best it can possibly be. Compare this to consulting, when you’re just trying to get it done before a deadline, instead of constantly refining and improving your product.

The biggest lesson that I’ve learned is how important a good support team is. At Cliniko we have a top-notch support team. If our customers could see the backchannel chat that happens, they would love Cliniko even more. We work so hard to make sure our customers get the practice management software that they need to make their lives easier.

It’s such a contrast from doing something just to get it done. I hate that so much. It would be difficult for me to go back to a consulting company after working for a product company.

So you’re much more diligent about the work you do now?

Yeah, it’s not about getting the work done quickly, especially at the expense of quality. We don’t give any timeline promises. We want the best code and whatever time it takes to do that, is the time it takes to release a new feature.

Not having meetings is a crucial part of that because you’re not interrupted while you’re on a roll. It makes me much more productive.

What is your workday like? The company is based in Australia, right? How does that work?

Yeah. The company is based in Melbourne, but we have people in Brazil, Canada, Poland, and the United States too. Our other designer, Kelly, just travels the world with his wife, which is really cool. We never really know exactly where he is consistently. He pushes code whenever he can get internet access.

The timezones were very tricky to adapt to and they initially bit me in the butt. It was difficult to adapt from the mindset of wanting feedback on a design before starting development, which is what I did while consulting. Whenever I would have an idea I would send Joel the comps and that would waste a lot of time while I was waiting for his response. I kept noticing that Kelly was just pushing code like mad and I didn’t understand how he kept up that pace.

Joel and I had a conversation about this and he told me to do whatever I think is right. Sure we might refine a few things, but I don’t waste time waiting for approval before I get started.

When do you work?

We have a thirty-hour work week. Our culture encourages a healthy work life balance, which I really appreciate. I remember saying things like, “My partner’s off today. Is it cool if I take the day off to hang out with her?” Joel would reply, ”If you’re not going to be working then don’t be online. It’s nice of you to ask, but if your partner is at home, spend time with her and just get the work done later.”

It can be hard to do a thirty-hour work week. Initially I thought that I’d have a lot more time for side projects, but when you get in a groove it’s hard to stop. I start around nine o’clock and hop off at five. Every once in a while I’ll skip a day here and there, but I usually work closer to a forty-hour week.

What feature of Cliniko are you most proud of?

I’m proud of our traction with getting it responsive. One of the reasons they hired me was to help get the product responsive and working on all devices. I’m really passionate about the responsive web. The progress that Kelly and I are making towards that end is going really well.

The calendar view is going to be a challenge.

Cliniko side navigation
A screenshot of the new side navigation that Derek worked on for Cliniko.

Yeah that’s going to be the most difficult. Kelly has done a really nice redesign, but I it’s going to be quite a task to build. The view on smaller devices is going to be challenging, but we’ll cross that bridge when we get there.

I just recently redesigned the navigation from being on the top bar with tabs to being a sidebar with a list. It’s going to work better responsively, especially with most laptops being 16” x 9”. It’s so much nicer to not lose those hundred pixels at the top.

Our customers don’t usually like change, but we posted a preview of it on Facebook and the feedback was much better than we expected. We thought that they would just roast us, but we had a lot of really positive feedback that motivated us to get the feature out sooner. We’re doing a lot of testing now to ensure that it works well. I’m really, really proud of the work we’ve done on it.

What are your interests outside of the web?

I try to learn a little bit of everything. I don’t like having people come do services at my house when I can do it myself, which usually involves me watching a lot of YouTube videos to learn. I really enjoy learning for the sake of learning.

I was constantly jumping around from job to job before I discovered web design. I worked at a motorcycle shop, on a production line, at a third shift factory job, as an installer of home theater systems, to car audio installation. I can also do remote starts and mechanic work too.

My primary hobby is what I do for work. I always say, “Coding and design is just a hobby. I just happen to get paid for it.”

Do you have any goals for next year?

I really don’t set goals because they are always changing. I never know what the next one’s going to be. Usually it comes up and I’m an extremely impatient person, so when something comes up, I usually try to hit that goal as fast as I can.