Product Designer at Swipies & Digital Ocean


CayleeBetts (Product Designer at Swipies & Digital Ocean)

New York-based all round designer who enjoys creating products and has an entrepreneurial flair.

New York, USA • January 5, 2018

What do you do?

By day I’m a product designer at DigitalOcean. By night and weekend, I sell a product I created called Swipies.

And work with some friends on a sports app called Scout.


What led you into design?

During my senior year of high school, a design college came into my Commercial Art class and I flippantly decided I’d go there. The cool thing about going the technical college route instead of a design program through a university is that I worked in Photoshop and Illustrator during my entire 3 years. When I graduated, I had a lot more technical skills than designers who got their degree through a university. As I get older, I frequently wish I’d gotten the university education and had the university experience (for example, my network from school is very small) but I’m also thankful I got to jump into the work faster. I got my first graphic design job for the Phoenix Suns when I was 18, still in school. I worked in the offices at the arena for a year, then I worked at a small design firm, and finally did an internship designing billboards for Clear Channel, all before graduating.

Describe your working environment

In the office, I’ve got a nice big sit/stand desk covered in Swipies with a view of the Freedom tower. By night I’m usually at my kitchen island switching between eating dinner, catching up with my boyfriend, packaging Swipies to ship out, and "laptopping".

What apps do you have in your dock?

Most used: Chrome, Slack, Sketch, Spotify, Zeplin, Sublime, Cyberduck, Hangouts. I now realise how much is here that I don’t need to look at every day.


What apps do you have on your iPhone?

Whoa, whoa, whoa — very presumptuous! Appears I am the lone wolf Android-using designer. ;)

I am a big fan of Google Translate and Google Maps when I travel, you can download the map and language of the city you’re in to use offline. I never use data when travelling, so these are super helpful. Headspace is something I’ve been trying but hasn't used much yet. Classpass. Pocket Casts. NFL Mobile (Go Seahawks). I use Apex Launcher and a couple icon packs to customise the appearance.


What’s your design process?

I’m working on our universal design process at DO right now. It can be tough to work in your ideal process if the company isn’t set up for that, so we’re trying to unify and formalise what allows us to do our best work. That way, we can advocate for getting allotted the time to do so. It’s been cool to see how each designer runs their projects, and how overall it’s pretty similar.

That being said, this is all fresh in my mind right now, so I’ll abbreviate what I’ve put together. As a note, I appreciate the double diamond method, and especially love this revamped version.

I think it’s important to always be thinking about the future of the product you’re working on, and to keep a list of ideas you can’t tackle right away. I also advocate for designer presence in roadmap discussions. If we spend our days thinking about the product, we should be present to help define what’s being built next.

At DO, after we kick off a project (or know it’s coming next) we hold a Design Studio, which is a structured 2-hour workshop that gets ideas flowing between people from different teams. After that, a project goes through a variety of research, user interviews, data and engineering kickoffs, and a session to draft a feature or requirements list for the MVP. At this point, I like to document v2 and v3 candidates and define what success we’d have to see with v1 to move on to v2.

Next, early work includes user stories or JTBD, sitemaps, flowcharts, sketches and wireframes. We’re trying to do more design jams (pairing with another designer) and talking to users more often and earlier on. Once we’ve got low fidelity designs, we go through a formal design review with the product design team (these are held every day for 30 minutes). More iteration and feedback gets tied in, I review with my vertical team, pair with an engineer to start planning how we’ll bring the work to life, and start heading towards prototyping and higher fidelity work. Another design review takes place once the work is further along. I loop back through any phases of the process as needed. Eventually, we send it out into the world. I like to keep an eye on any design bugs to report and watch the data we’re tracking. Then we look toward v2 or making any changes to what went live.

What do you use to plan initial design concepts?

Design Studios, as mentioned above, are awesome for getting started. From there, I use Google Spreadsheets and Docs for planning, Swipies for sketching, and I export Sketch wireframes to Zeplin for discussion and feedback.

What pieces of work are you most proud of?

Swipies, for sure. As a product designer, I think it’s rare to get to work on a physical product that does really well. I think it’s the one truly unique thing I’ve done, and I’m really proud of the success they’ve had so far.

Where do you go to get inspired?

Travel is such a solid reset. If you let yourself get away from your day-to-day thoughts, it’s amazing to see what resurfaces first when you return. I think it’s a great way to choose what to focus on next.

Also, I get really inspired by other entrepreneurs, so I’m more into Shark Tank and entrepreneurial podcasts than going on sites like Dribbble. It’s a great tool when I have to stumble my way through visual design, though :)

What apps do you use when designing?

Sketch as much as possible. Sometimes Illustrator when I want to do an icon or something more visual. I despise working between the two though; they don’t play nice. I like Zeplin for feedback within my team and for engineers to pull styles from. I don’t use InVision much lately, but I think it’s valuable in some cases. Chrome DevTools gets a lot of use when I’m fine-tuning work that’s in staging. Sublime Text.

How do you go about testing your design or gathering feedback?

In terms of research and customer feedback, I created a scrappy, 12-page ‘Informed Design Framework’ for our team at DO, attempting to start the documentation of methods we can use to validate our work, when each should be used, and the resources we have to execute it all. As a small, growing team, we would love to do so much more. It’s super hard to do research well without a dedicated team member, someone that’s way more experienced and focused on that work. With that being said, since joining DO, I’ve done customer surveys, held user interviews, watched our customers using our products on FullStory, and sought plenty of feedback across teams at DO. Other designers have had the ability to release betas and do more involved usability testing as well.

In terms of internal feedback, we have a daily design review meeting with the whole team. We have a dedicated feedback channel on Slack. And I personally work super fluidly with my product team via Zeplin and Slack to get feedback as I design. We’re also encouraged to do design jams with other designers regularly. So there are several avenues for receiving internal feedback.

With Swipies, I send free samples in exchange for feedback. I also follow up with every single customer. I’ve done some surveys asking people which products they’d like to see next, and it’s cool to go back and tell those people when you’ve listened. They’ll generally buy right then.

What music do you listen to when designing?

None! Ever. I can’t think and listen to music at once. I’ll try to listen, but 6 hours later I’ll realise I paused the first song to think and never put it back on. Photo editing is the only thing I can do while listening, and that’s because I hate doing it and need to pass the time. I spend a lot of my day collaborating, talking, emailing, reading/researching, sketching, and only the minimum necessary time executing in Sketch. I like do a lot of pre-work and then execute quickly. All that pre-work requires quietness for me.

What’s a great website for inspiration?

Honestly… Twitter and Medium. Great starting point for seeing what everyone is up to.

How do you keep improving yourself as a designer?

Pursuing anything I am curious about. Learning more about business and the technical side of things — learning to build my own stuff, and understanding how the internet actually works.

Why did you join your company?

The people.

What’s it like working at your company?

I feel more enabled and trusted than I have in a role before. It’s also a really social, fun, caring environment. We’re also super spoiled in terms of activities and perks, which is new and fun.

What design challenge do you face at your company?

Dealing with tech debt is hard. We’ve got a product that was originally built by an external product shop that has made it super hard to move fast. So we have had to make some temporary sacrifices to keep things moving forward at a decent speed.

How do you handle design disagreements at your company?

I love the “give a shit” scale. I think I first heard about this on Design Details in their early days. If you feel one way but you only rate yourself 💩 2, and your co-worker rates 💩 8, you’d move forward with their idea because they feel more strongly. The thing that makes this work is that when you’re working with super smart people (like I do) and you trust them (like I do) you’ll be fine either way. Unless they’re wrong. Then there’s data for that ;)

Is your company currently looking for designers?

Yes, we are!

Any tips on designers getting a job at your company?

Be yourself. Take your time on the design challenge. Show your process in your portfolio and the challenge. Tell us what you want to learn. We look for designers who are focused on product thinking and solid UX, but we don’t accept designers without strong visual skills to match. The ability to code is also important, but a willingness to learn tops that. We’re looking for pretty senior designers right now.

What product have you recently seen that made you think this is great design?

I’m loving Headspace so far. Also really into Sherpa in terms of the service it offers. I tend to rave about products that make my life noticeably easier or better.


Do you have a cool design trick/hack/shortcut?

Definitely a keyboard shortcut user and like to share tricks I’ve learned with co-workers. I’ve converted a few people to Sketch by showing them great shortcuts. The only design trick I can think of is my method for converting Swipies sketches or illustrations to vector super fast. I should really make a little video…

Any advice for ambitious designers?

If you want to do more user research or front-end work or prototyping or illustration (whatever it is) but can’t fit it into the process at your current company, start a side project and bring your ideal process to life. Do the things you’re curious about. It’s too easy to accept a non-ideal work situation and wait it out. But when you get to your next interview (and you’re trying to up-level) and they ask you about your experience, it’s going to sound so much better to say “I haven’t been able to do that in my past roles, so I started a side project to learn more about it” than “I don’t have that experience.”

Also, if you’re just starting out, immerse yourself. Go to events, follow people on Twitter and keep up with what they’re doing, ask questions, read, listen to podcasts. You’ve got to really care and be engaged to accelerate your career. Once you’ve landed the type of job you’d been dreaming about, get better all the time. Expand your skills and write about your work and your process (it’s the best way to clarify your opinions).