Design Hiring FAQ

Below is a list of frequently asked questions we have received from candidates. Have a question that isn’t listed here? Get in touch!

How we work
Design careers and growth


How many steps are there in your recruitment process, and how long does it take to complete the journey?

The hiring process includes a combination of async and sync conversations and a design trial, coordinated to ensure a smooth process for every role.

Automattic’s hiring process includes a paid trial project. If chosen for a trial, you are given a project you can work on as you have time. We use these projects to see how it is to really work with each other: for us to see how you approach a problem, and for you to see how we communicate and collaborate here at Automattic.

What does the design trial look like? What level of commitment are you asking for?

For trials, we set up a P2 (internal blog) where we post the brief that outlines the project and its goals. Candidates are also assigned a “trial buddy” who is an Automattic designer and is responsible for providing feedback and guidance during the trial.

The trial brief breaks the project into different stages, one for problem definition and solution exploration, another for wireframes/flows, and a final one for high fidelity/prototyping.

We generally suggest candidates spend about two weeks on trial, but when you work on it is up to you and your schedule.

You can read more about our trial experience here.


Which team or project will I be working on? Are you recruiting for a specific product?

Our hiring team for design is centralized, which means we can assess needs and fit for all positions. After a candidate successfully completes a trial and is hired, the hiring team makes recommendations for roles within Automattic that best fit with their skills, experience, and goals.

Does the employee have a say in how they’re assigned or utilized?

Different areas across the org have specific talent needs. As a person works through the recruitment trial, we analyze strengths as well as areas of improvement, then come to a recommendation based on their overall performance during all recruitment steps.  After six months on the team, a designer  may request a rotation to another team. In terms of projects within the team, yes, you could ask for a change if the project doesn’t feel like the right fit. One of the cool things about Automattic is that team switches are encouraged. So, if where you land when you’re hired doesn’t end up working out, there are many more opportunities to try within other teams.

How are teams built? Is it geographically? Time zone?

Teams are built following the needs of the business unit and the characteristics and capabilities of each contributor. Also, teams might change with time. As we work asynchronously (“async”), location and time zone are usually not considered when assigning an individual contributor to a team. 

How many designers are in Automattic, how is the team structured?

There are currently just over 80 people in the Design org, including our Design Council, led by Pablo Honey and Kelly Hoffman. 

The Design Council is our design leadership team, focused on guiding Design Directors and bettering the impact of design for Automattic as a whole.

Designers work within business units or divisions; we use the term interchangeably. Most business units are correlated with a product, like WordPress, but we also have designers on teams like Marketing and Talent. Designers have the opportunity to rotate to different teams to gain new experiences.  

This number also includes our Designer Experience team, currently with 7 team members, who oversee the experience of designers working at Automattic. 

How we work

How does the typical day of a designer look at Automattic?

It depends, as it varies with the team. We’re also a choose-your-own-adventure type of company. This means you can help define what work would be the most impactful and plan your agenda dynamically based on ad-hoc needs. In this article, you can read more about how our designers organize their daily work.

How is the design team collaborating?

Within design teams — teams typically have a weekly hangout call for reviewing work and giving feedback. Teams also have their Slack channels where they share in-progress work for feedback throughout the week. Design iterations get posted on P2 for further feedback. 

Within the design org — this is an area that we’re always working to improve. We’ve implemented “Design Snaps”, where, every other week, each team posts to our Designomattic (Design org) P2 with recent work. It’s a great way to get, at a regular interval, a snapshot of what other teams are doing. 

How does the team communicate usually?

Each team is different, but we try to communicate async as much as possible, because teams often have people across many different time zones. For standups, teams like to do them async in Slack.

Each team usually also has a weekly video call to meet face to face and discuss projects, priorities, and to get to know each other.

Are the teams usually working in sprints? How are projects managed? Are there project managers?

Again, it depends on the team and how they organize their work. Some teams employ agile methodologies, while others have developed their own custom approach.

Are the Product Designers usually working with data? Do we have data analysts?

We assume all Product Designers have a basic understanding of and ability to manage data. How do we work with data? There isn’t just one way: the methods and tools are endless. It really depends on the team and their capacity.

How do designers work with the users regarding interviews and testing? Is it also async? Do we have a research team that supports Designers?

Each team usually runs user testing sessions following their preferred methodology and tools. Sometimes teams do 1:1 interviews, and sometimes they use a survey or other quantitative methods. We don’t have an official user research team. As a design org, we are considering expanding the team with a dedicated research squad, but we don’t have a clear roadmap to do so for now.
Suggested reading from our Design Blog about this topic: Recruiting participants for remote user tests.

Design careers and growth

What kind of career perspectives are there at Automattic? What can I achieve during my career in the Design team?

We want to empower designers to do impactful and interesting work here at Automattic. Designers have the opportunity to rotate to different teams to gain new experiences and skills, and our flat hierarchy provides a lot of autonomy to designers to shape their own careers and contributions. That flat hierarchy also means that we don’t have a formal career ladder per se, but as we continue to grow quickly, new opportunities will arise to contribute to many long-term, strategic projects. 

We offer a lot of career development support to guide career journeys, including mentorship, coaching, peer learning programs, and the opportunity to engage in additional outside professional development opportunities like books, training courses, and workshops. 

Does Automattic have a formal career ladder or path for designers?

We don’t have formal career paths or a ladder for designers at Automattic. We have designers (ICs) and design managers. So, we don’t formally do L3 / L4 or Staff titles, or things like that. A flat hierarchy with more autonomy at all levels is very important to the team.

That being said, there are opportunities for designers who are keen on leadership. Our teams are scaling up quickly, and we’re tackling many long-term, strategic projects. 

Would Automattic provide a mentor or guidance if someone wished to be career-progressed to a leadership role?

Yes! Our design mentorship program pairs designers thoughtfully, based on their goals or ambitions. In addition to leadership, mentorships focus on things like communication and presenting your work. We also offer an executive coaching program that pairs Automatticians with professional coaches to help them achieve their goals and build skills. There are many opportunities for designers who are keen on leadership. Our teams are scaling up quickly, and we’re tackling many long-term, strategic projects. 

How do you share feedback? Do you have specific design crits or structured feedback sessions?

Each team has its own rituals. For example, some teams have product focus design crit (weekly) and team-level critiques (weekly). We also promote async feedback, where people can share work in progress on Slack or P2 to get additional feedback. 

In general, we have a very strong feedback culture where anyone can share their voice. For example, for design, we post iterations to P2 for our colleagues to give us feedback on. The expectation is that you will give your teammates a fair amount of time, ideally within 24-48 hours, to review your work and provide feedback. There’s no expectation of receiving feedback immediately, as you would in a synchronous environment. The result is that feedback is meaningful and considered, not knee-jerk and reactive.