Automattic Design FAQ

The hiring process consists of asynchronous and synchronous conversations. If these go well, we’ll invite you to complete a paid trial project.

The trial project is something you can work on as you have time. It’s an opportunity for us to see how you approach a problem, and for you to understand how we communicate and collaborate here at Automattic.

Design trials take place on P2 (our internal blogging system) and on Slack. You’ll receive a brief outlining the project and its goals. You’ll also be assigned a buddy who is an Automattic designer. Your buddy 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 suggest limiting your time on the trial project to one week, putting in about 8-12 hours total. Exactly how and when you schedule that is entirely up to you.

Read more about Automattic’s hiring process here.

AI and augmented design proficiency is assessed at every evaluated stage of our process and it’s a requirement for both Senior Product Designer and Brand/Creative Designer roles.

We look for designers who build end-to-end workflows that connect research, design, code, and automation into cohesive flows — and who can document and share those practices with others. Candidates who reimagine how design work operates and define practices that scale across teams are a strong hire.

Candidates still exploring and not proficient with those tools are not a match for our current bar.

During the interview process, you’ll be asked to share concrete examples: specific tools, specific workflows, and what changed as a result. During the trial, coded prototypes built in AI-assisted environments such as Claude Code, Cursor, or Lovable carry more weight than static mockups, and we ask you to document your augmented workflow alongside your design decisions. There’s no checklist of approved tools:  what matters is that AI is genuinely part of how you work.

Yes, active AI experience using LLMs and AI prototyping tools is required. Starting from March 2026, we added AI & Augmented Design Practices as a formal requirement for all design roles, updated our job descriptions, and introduced an AI-focused screening question at the application stage. Candidates with zero demonstrated AI experience are not moved forward.

“Augmented design” at Automattic means integrating AI, automation, and code-assisted tools into the actual design work. For product designers, this might mean using AI to accelerate research synthesis, build interactive prototypes faster, or explore a wider range of solutions in less time. For brand and creative designers, it might mean generating scalable visual systems, adapting assets across formats, building small scripts that support production, or using AI to prototype landing pages that would otherwise require costly photography or illustration.

We expect AI and new tools to expand what designers can accomplish and improve how they collaborate with engineers and other stakeholders. We’re also interested in designers who share what they learn. Teaching, mentoring, and documenting effective AI workflows are explicitly part of what we look for and expect from designers once they join the team.

We want AI to be part of how we design, not a separate practice layered on top of it. The expectation for all designers on the team is that AI, automation, and code-assisted tools are integrated into their actual workflow.

In practice, this may look different depending on the role, the team, and the project. Product designers might use AI to accelerate research synthesis early in a project, generate interactive prototypes with tools like Claude Code, Cursor, or Lovable to test ideas before committing to high-fidelity work, or explore a wider range of solutions within a sprint than would otherwise be possible. Brand and creative designers might use AI to develop scalable visual systems, rapidly adapt assets across formats and channels, prototype landing pages, or automate repetitive production tasks.

What’s consistent across the team is the expectation to share. Designers who develop effective AI-assisted workflows are expected to document them, write about them on P2 (our internal blogging platform), and help teammates adopt new practices — that’s part of how we contribute to Automattic Design as a whole: we’re building a team where every new designer meaningfully advances how design work happens here, not just in their own projects.

Designers at Automattic are hired in a centralized fashion, meaning we’ll assess you for every open position to find the best match.

Based on the results of your successful trial project, the hiring team makes a recommendation that most closely accords with your skills, experience, and goals. We believe this is the best way to set you up for success at Automattic.

As mentioned above, we’ll assess you for every position and find the best match. If, after six months on a team, you don’t feel like it’s the right fit, you can ask for a rotation to another team, or a team switch.

Rotations, which typically last 3-6 months, are encouraged at Automattic to build experience across teams and products. Team switches offer reassignment to another team that needs your skills.

We assemble teams to best serve the goals of each business unit, taking into consideration the talent and capabilities of each designer. As/when business goals change, we reassess the teams to ensure we have the right complement of designers. Since we work remotely, in a distributed and asynchronous way, geography and time zone usually do not play a large role in how teams are assembled.

There are currently just over 70 designers working at Automattic. Designers work on teams and/or squads within business units that typically align with a product, or collection of products. At the moment, we have ten design teams, with varied squads within them.

Automattic Design, tasked with guiding team and squad leads and bettering the impact of design for Automattic as a whole, is led by our Design Council (DC): Pablo Honey and Kelly Hoffman.

Automattic Design is supported by the Designer Experience team, tasked with providing a strong onboarding experience, rich learning/professional growth programs, and fun and inspiring culture and community programs. Read more about the Designer Experience team.

Everyone at Automattic is encouraged to set up their workday to best suit their individual needs, while providing value and impact against our goals. We expect designers to spend most of their time doing design work, and keeping a steady pace of shipping projects. In this article, you can read more about how one of our designers organizes their daily work.

Design teams typically have a weekly call to review work and give feedback to one another. Teams also have their Slack channels and project tracking in Linear.app, where they share in-progress work for feedback throughout the week. Design iterations are posted on P2, our main communication tool, for further feedback. Anything shared on P2 is open to collaboration and feedback from anyone around the company, in fact, it’s encouraged.

Within the Design Org we’ve implemented “Design Snaps”, where, every other week, each team posts their recent work. It’s a great way to understand what all teams are working on, and to recognize and celebrate contributions.

Some suggested reading about collaboration: Diversity in Ideation, We’re Stewards, Not Owners: User Experience and Open Source.

Communication is oxygen at Automattic.

Generally, we communicate asynchronously, in written form, as much as possible given that most teams have people spread across many time zones around the world. Even standups are often done async in Slack. Weekly synchronous video calls are used to discuss projects, priorities, and to get to know one another.

Some suggested reading about communication: How to Be a Neurodiversity Ally, Build effective remote design teams with the right communication model.

Teams organize their work in various ways to best suit their projects. Some teams employ agile methodologies, while others have developed their own custom approach. Roles on teams are equally varied based on team needs.

At Automattic, our product designers are expected to have a basic understanding of using and managing data to inform their work.

Designers have access to dashboards and team‑specific data sources, leveraging various methods and tools. We foster a collaborative environment where designers can work with data professionals from other teams within the company.

We encourage designers to be independent in exploring and researching data. While they have access to relevant data, we expect them to proactively seek and analyze it to make informed design decisions. This approach fosters a more effective design process within our organization.

Teams run user testing sessions with their preferred methodology and tools. Sometimes teams conduct 1:1 interviews, and sometimes they conduct surveys, or use other quantitative methods.

The design organization does not currently employ a dedicated research team. We are considering expanding the team with a research squad.

Some suggested reading about design research: We’re all ears, Building a Process for Design Research.

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

In general, we have a strong feedback culture where anyone can share their voice. In Design, we post iterations to P2 for our colleagues to provide feedback. The expectation is that you will give your teammates 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.

Automattic is a “choose your own adventure” workplace, where work that makes an impact is most important. It’s not about what your title says, but about what you do. You’ll have lots of autonomy to shape your career and your contributions to best use your talents and skills.

Opportunities to learn and grow abound, from team rotations, mentorship, coaching, peer learning programs, or professional development through books, training courses, and workshops.

We don’t operate with the traditional career laddering approach, and maintain a flat organizational hierarchy. This means that we’re adaptable and nimble, able to quickly adjust teams to take on challenges. As we continue to grow, we expect to have opportunities for anyone to take up lead positions, to lead projects and initiatives that have strategic impact.

Yes! Automattic provides professional career coaching to all employees to help set and accelerate professional goals in a confidential and supportive environment. The Designer Experience team also offers a design mentoring program that pairs designers in a thoughtful manner that benefits both the mentee and the mentor.

Our internal Learn team also offers myriad courses, coaching, workshops, and training on many topics, including leadership.