Reimagining the Design Interview with Jay Sylvester, Rockerbox's Newest Product Designer

June 8, 2022
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Reimagining the design interview

The UI/UX design process can be infamously rigorous and drawn out as both sides struggle with the broad and varied skill set that successful design candidates typically possess.

In a previous post we broke down some issues with the standard design interview process and offered strategies to address those problems. We wanted to take this conversation a step further, so we reached out to the experts we trust most: candidates and hiring managers interviewing on

We spoke to Jay Sylvester, an Underdog candidate who was recently hired on our platform, to get his take on what makes an effective and empathetic design interview process.

Q: Before we dive into your experience interviewing with Rockerbox, can you tell us a bit about your experience communicating with companies on Underdog?

A: I stumbled on after looking for a platform that would help make job searching a little more manageable. I like that I didn’t have to fill out a bunch of different applications and that companies could directly reach out to me. So my experience talking to companies on Underdog was exactly what I was hoping for - quick and easy. My profile was up for less than a week before I was having multiple conversations with companies. The companies were all communicative and seemed more willing to move quickly than on other platforms I’ve used.

Q: So you recently started a position as a Product Designer at Rockerbox. What was different about Rockerbox’s interview process? Is there anything you especially enjoyed?

A: There were tons of things I loved about Rockerbox’s process. Design interviews are generally slow and intense so I was expecting a process with unrealistic scenarios and weird code. Right off the bat, Rockerbox impressed me with how quickly they moved. They reached out to me within my first few days on the platform and seemed excited to move the conversation forward.

The interview process was conversational and honest. It’s an interview so there was a level of formality but mostly it felt like a great conversation with people who understood the business needs. The general tone made me feel comfortable asking questions and being frank about what I was looking for in my next role.

Their design exercise is one of the things that won me over. Some companies use the design exercise as an opportunity to unethically obtain free work from design candidates. Rockerbox was thoughtful enough to create a design exercise that wasn’t directly related to the business, but they also understood the role enough to create an exercise that allowed me to showcase my skills.

Q: It's rare to hear of design exercises that are effective for both the hiring manager and designer. Can you tell us more about what specific parts of the design exercise won you over?

A: There were three main actions that Rockerbox took that made it clear that they would be a great place to work:

1. They gave me time to prepare. Before the design exercise, they shared the parameters of the exercise and the objectives that I would be evaluated on. This showed me that they understood the real world skills I would need to excel in the role. I would never walk into a new client's office without completing my prep work, so having the time and resources to prepare for the design exercise helped put me at ease.

2. They focused on the process, not the results. Design is not a process that can be done within an hour or however long a design interview lasts. It’s also not a process that is done in silos. Standard design interview processes put a ton of pressure on designers to produce something beautiful and hi-fidelity during a short amount of time. Rockerbox focused on my personal design process and the approach I took to solving defined problems. I never felt like I had to produce a finished product because the goal was to show off the process I’ve refined over years as a designer.

3. They were honest. The main selling point of Rockerbox’s interview process is that they never tried to ‘sell’ me on the team culture. Everyone from the CEO down had super positive attitudes. They were frank about company challenges and were honest about the kind of person they needed in the role. Their willingness to be open and honest made the whole process smoother and easier than most others.

Q. To wrap up, what would you say to candidates and hiring managers struggling through a stressful design interview process?

A: To candidates, I would say to try not to put a ton of pressure on yourself. Remember that this is a conversation and is equally about what you are looking for in your next role. Don’t be afraid to ask questions or push for more information. You know your stuff and you have a personal point of view - be confident in the skills you’ve developed.

To hiring managers, I would say to remember that talent, capability and the ability to learn and grow are all more important skills to assess than hyper specific domain knowledge. Classroom UX is very different from real life UX so remember to give candidates a chance to show you what they are capable of.

If you’re ready for your next design role, click the button below and sign up in 60 seconds. We’ll put you in front of hundreds of pre-vetted tech companies and you could be halfway to your own seamless design interview in just a few days. Apply here.

Rockerbox is hiring!

Rockerbox is a marketing data analytics company that helps brands understand the key drivers behind their growth. From paid to organic and digital to offline, their marketing measurement platform gives growing DTC e-commerce brands the insights they need to win.

Our philosophy is that interviews are a two-way exploration to help us understand whether we’re likely to have a mutually positive experience working with a potential Rockerboxer. Although interviews are structured differently depending on the role we’re hiring for, we strive to cover the following areas for everyone we interview:

Is this person interested in where Rockerbox is going, and motivated by the opportunities we see? Do they have the skills they’ll need to be successful in the role? Are our values a match for how they like to operate?

Our goal is to take candidates through an interview process that gives them the ability to showcase their capabilities while also providing an opportunity to evaluate whether Rockerbox is the right fit for them. In general, prospective Rockerboxers are interviewed by their future manager and colleagues, as well as other people who may not be on the same team. For the Product Designer interview, we’ve created a hands-on interview exercise to represent, as closely as possible, what a working session looks like on the job. We want prospective Rockerboxers to very clearly understand what it will be like to work with us, and to be excited at the idea of building together.

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