Director of Designer Experience-Automattic

September 1, 2021

Job Description

At Automattic, we believe in making the web a better place. We’re the people behind, WooCommerce, Tumblr, Simplenote, WordPress VIP, and more. We’re looking for a Director of Designer Experience to join the Automattic team! This is a leadership role requiring a holistic understanding and view of team member growth and development, with an aim towards robust onboarding, skills-tracking, and education programs that support both individuals and the business needs.

You’ll join our Designer Experience team — Automattic’s version of Design Operations — in our mission to build an outstanding experience for all designers at Automattic. DesignEx (as we affectionately call it) is responsible for Designer hiring strategy, onboarding, culture and community, growth and development, and design infrastructure (systems & processes). Reporting to the Head of Talent Acquisition you’ll be a part of a group of managers who are responsible for recruiting, onboarding, and various aspects of learning and development within Product Design, Customer Support, General Business, and Engineering.


  • Strategic Leadership: Working in partnership with our Design Council (Design leadership) to develop the strategic direction for hiring, onboarding, performance, growth, and community for Design at Automattic.
  • Team Planning: Team goal setting, prioritization, and direction for team members where appropriate as they develop their various programs.
  • People Management: Managing the DesignEx team members, giving feedback on their work and performance. Building out the team as appropriate based on company growth and needs.
  • Design Org: General stakeholder management with the organization and function we support as a team, communicating with our Design Council, our Design Directors, and larger design org. Advocate and facilitator for members of the design org in need of counsel. Consulted on various people decisions, including hiring calls, team placements, performance situations, and team switches.
  • Talent Acquisition Leadership: Coordinate with the talent ops leadership team to ensure collaboration, consistency, and shared knowledge.
  • Hiring Strategy: Identify high priority talent gaps across the organization, with an eye for building cross-functional, resilient design teams that can handle any type of project thrown at them. Lead all aspects of Design Hiring to ensure we’re attracting, hiring and retaining the right talent. Collaborate with Design Recruiter(s) to improve processes and candidate experience.


  • Stakeholder management across teams / divisions.
  • Mentoring and supporting team members and leads to feel successful.
  • Expectation setting and performance management.
  • Educational programs, onboarding and career growth.
  • Community building and engagement.
  • Big picture planning and direction to help ensure forward momentum and ability to communicate this consistently.
  • A strong focus on people, what makes a great workplace for them, and how that contributes to producing great work.
  • Zooming in and out, and bridging between strategy and execution.


We’re a global, distributed workforce in over 70 countries. We value open source, prioritize transparent communication, believe that good ideas can (and do) come from anywhere, so we encourage Automatticians to work together across positions and roles. Together we create, develop, and care for a collection of digital products and services that are committed to democratizing publishing and commerce.

  • We’re kind to each other and our users – we strive to build a positive, supportive, and inclusive culture of cohesive teams focused on delivering value to our customers.
  • We have no set hours, or expectation that you’re online from 9 to 5. You create a schedule that allows you to get your best work done.
  • We travel sometimes to meet up and work together.
  • We welcome collaboration, and you can be involved in any discussion across our many communication channels. Here’s more about what we expect from ourselves.


If you’d like to apply, fill out our application form below.

We are lucky to receive many applications, so try to make your application stand out.


We are the people behind WordPress.comWooCommerceJetpackTumblrSimplenoteLongreadsDay One, and more. We believe in making the web a better place.

We’re a distributed company with more than 1600 Automatticians in 80+ countries speaking 90+ different languages. We democratize publishing and commerce so anyone with a story can tell it, and anyone with a product can sell it, regardless of income, gender, politics, language, or country.

We believe in Open Source and the vast majority of our work is available under the GPL.


We’re improving diversity, equity, and inclusion in the tech industry. At Automattic, we want people to love their work and show respect and empathy to all. We welcome differences and strive to increase participation from traditionally underrepresented groups. Our DEI committee involves Automatticians across the company and drives grassroots change. For example, this group has helped facilitate private online spaces for affiliated Automatticians to gather and helps run a monthly DEI People Lab series for further learning. Diversity, Equity and Inclusion is a priority at Automattic, though our dedication influences far more than just Automatticians: We make our products freely available and translate our products into and offer customer support in numerous languages. We require unconscious bias training for our hiring teams and ensure our products are accessible across different bandwidths and devices. Learn more about our dedication to diversity, equity, and inclusion and our Employee Resource Groups.