Head of Web Engineering

As a Head of Web Engineering you will be responsible for the technical alignment, project coordination, and technical execution within that aligns with our organization's business goals. You will refine and manage engineering efficiency by implementing new processes, metrics, and ideas for engineering improvements, understanding where new products and tools are needed or acquisitions required. 

You are motivated by impact, whether that’s achieved by rapid deployment of features to assist users, helping merchants to run their business on, or working with high-profile developers to ensure they get the most out of the ecosystem.

Your style is to proactively get things done while reducing friction for your colleagues and customers and to respond rapidly when called upon. You collaborate as an aid to our users and pride yourself in producing quality code. You enjoy managing requirements, and enjoy collaborating with members in various roles across organizations.


  • Own the product interconnectivity, creating a seamless ecosystem of Automattic products into one end user experience.
  • Create and manage a technical roadmap for, aligned with the product vision.
  • Map the technical feasibility and ensure technical alignment between divisions; apps, marketing, design,
  • Develop operating metrics to enable teams to ship and test effectively and efficiently. 
  • Help design process standardization that enables the team to scale, including velocity management and capacity planning.
  • Implement and manage changes accordingly, ensuring division goals are achieved or issues are unblocked. 
  • Create a strategic technical vision, understanding where new products/tools are needed or acquisitions are required. 
  • Manage a large, distributed, multi-level engineering team.
  • Organize and prioritize initiatives in accordance with’s goals and objectives. 
  • Think and execute globally, ensuring the right visibility within our community and our products.
  • Coordinate and execute on all communication, from monthly business reviews to release management. 


  • Hands-on experience in back-end and front-end development.
  • Work experience as a head of engineering or in a similar senior-level position.
  • Working knowledge of web technologies, and familiarity with web content management platforms/website builders, SaaS, and open source.
  • A clear understanding of business fundamentals and a familiarity in working with product data and business metrics.
  • Experience working cross-functionally with a wide range of teams. 
  • You are an excellent communicator (written and verbal), detail-oriented, very well structured, with a passion for creating processes. You are highly self-­motivated and able to work with significant autonomy.
  • Experience in working in a remote environment is a plus.

This role will report to the Chief Experience Officer.

About Automattic

We are the people behind, WooCommerce, Tumblr, Simplenote, JetpackLongreads, Day One, PocketCasts, and more. We believe in making the web a better place.

We’re a distributed company with more than 1800 Automatticians in 96 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.

Diversity, Equity, and Inclusion at Automattic

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.

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All Jobs Require

  • Great communication skills. We’re a distributed team, so frequent and clear written communication is a must.
  • Self-driven work ethic. You need to be a self-starter who loves taking initiative and seeing things through to completion.
  • Curiosity and the desire to learn. Our business is changing and growing fast, who knows what will be the skills of tomorrow? Flexibility is key.
  • Ability to Travel. We value those rare occasions when we meet our colleagues in person. Normally, we require 2–3 non-consecutive weeks of travel per year, usually by plane. Currently, company travel is limited, and travellers must be vaccinated. All travel is optional for now. We’re continuing to explore new, remote ways to stay connected.