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Head of Engineering



True Search has been retained by Automattic (the creator of WordPress.com) to fill a key leadership role. We are looking for a Head of Engineering to support our high-growth business. The successful candidate will report to WordPress VIP CEO, Nick Gernert.

Successful Outcomes

  • Unify a cohesive ‘Engineering Vision’ across the organization.
  • Scale robust product delivery teams, and ensure ongoing delivery from product engineering.
  • Optimize delivery from Engineers on the Support team, prioritizing long-term thinking to solutions over short-term bandaids for individual customers.
  • Plan and execute strategy on key initiatives. Lead the view on the long term roadmap and work closely with leadership to set product vision as part of three-year plan, board updates, etc.
  • Manage strategic technology vendors and their place within our offerings (i.e. GitHub, New Relic, etc).
  • Balance across past, present, and future commitments.
  • Help enterprise customers solve business challenges through WordPress in ways that can be marketed as a key differentiator.
  • Oversee Hiring, Onboarding, Career Development, and Team Structures.
  • Develop external communications focused on customer and community communications related to areas such as product updates, service status, security, etc.


The Head of Engineering must be a highly strategic leader able to play a meaningful role in the growth of the business and development of our product capabilities. This role is multifaceted, from new product development to systems engineering and servicing external customers, working with Engineering Operations (deploying, supervising, and defending), but also on the Development side (architecting, building, and deploying). We are seeking someone who:

  • Deeply understands opportunities with regards to Digital Experience Platforms and Enterprise CMS.
  • Is comfortable operating at the executive and board level in a fast-growing enterprise software business (which always has some degree of ambiguity and change), and adept at building effective relationships with key strategic leaders.
  • Is a hardworking player/coach with strong technical capabilities and a willingness to “do the work” even if the primary expectation is that they’re not an individual contributor.
  • Can build and maintain great partnerships with other leading technology organizations.
  • Is a low-ego and outcome-focused leader who is inventive and comfortable delivering with what is currently available.


  • Demonstrated ability in a high-growth technology company that was able to achieve significant growth, where they were responsible for setting the overall technical strategy and lead all software development for the organization.
  • Ability to implement and scale modern SaaS development practices to ensure the highest quality software is delivered to customers in a reasonable time.
  • Experience defining and achieving target metrics and achievements for product & platform delivery.
  • Have significant experience building enterprise-caliber products from inception and scaling their usage.
  • Has a love for solving complex problems with simple solutions, and (preferred) expertise with technologies such as NGINX, Docker, PHP, Golang, LUA, MySQL, ELK.
  • Deep domain expertise across SaaS-based Enterprise Content Management, Digital Transformation/Experience, and/or Marketing Technologies.
  • All VIP and Automattic team members are distributed. Effective communication in written form is important, along with the ability to empower teams and build confidence across a distributed environment.


  • Open vacation policy (no set number of days per year). We encourage all employees to take the time they need for vacation, to pursue their own interests, to stay healthy, and to spend time with friends and family.
  • Home office setup and coworking allowances. Working from a coffee shop? You can use your coworking allowance for the requisite latte!
  • We happily provide or reimburse hardware and software you’ll need, as well as books or conferences that promote continued learning.
  • Company-sponsored life insurance.
  • Open parental leave (includes maternity, paternity, and adoption). If you’ve been with Automattic for 12 months, your leave is fully paid.
  • WordPress-branded laptop at your four-year anniversary. A spiffy set of wireless headphones at your seven-year anniversary.
  • Paid two to three-month sabbatical encouraged every five years.
  • We cover all costs of company travel, so dust off that passport! Your team will get together one to three times per year in locations around the globe.
  • Other benefits are country-specific, and include health, vision, and dental insurance; matching retirement/pension contributions; childcare vouchers; income protection; travel insurance; and discount offers.

Diversity & Inclusion

We’re improving diversity 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 D&I 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 D&I People Lab series for further learning. Diversity 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. Read more about our passion for diversity and inclusion. Read more about our dedication to diversity and inclusion.

How to apply

Let us know what you can contribute to the team. Include the title of this position and your name in the subject. Proofread! Make sure you spell and capitalize WordPress and Automattic correctly.

Deadline for applications: 18.10.2020.

Job listing has been deactivated.

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