Automattic, the company behind WordPress.com, Jetpack, and WooCommerce, is seeking an exceptional person to help us execute on the first line of our creed, I will never stop learning.

As Chief Implementor, Learning and Development you will lead efforts to educate and upskill Automatticians across more than 60 countries, evaluate the effectiveness of our existing programs, and drive the creation of new ones to help us meet our business needs and ensure that every Automattician is always growing. This is an opportunity to coordinate and execute what we already have in place, as well as spearhead new programs to support Automattician development and growth.

In this role you will:

  • Oversee Automattic’s extensive coaching program of around 20 coaches.
  • Evaluate our new lead “101” training cohort program and assist in crafting the 201 and 301 versions of it.
  • Make sure that our internal intranet represents the best of what we want people to learn and understand, and that whatever can be is published here on Automattic.com as well.
  • Understand and advocate for what distributed work changes about what we do, where we are different and where we should operate more like a non-distributed company.
  • Track the effects of personal development in contributors and leaders in business results.
  • Gain a deep understanding of Automattic’s operations and culture and develop a program for tracking and creating learning and development opportunities across our extensive support operations and other highly dynamic roles.


  • Have been responsible in the past for the growth and results of an organization.
  • Have a working knowledge of web technologies, and familiarity with web content management platforms/website builders, SaaS, and open source.
  • Are conversant in the latest and greatest in personal and organizational development literature.
  • Comfortable managing across roles, divisions, and reporting lines.
  • Are a voracious reader.
  • Have excellent communication skills and are an effective writer. Not afraid to produce lots of written content yourself.
  • Are highly self-­motivated and able to work with significant autonomy.
  • Love the open internet and all that it stands for.

We’re serious about growing diversity in the tech industry. We want to build Automattic as an environment where people love their work and show respect and empathy to those with whom we interact. Diversity typically includes, but is not limited to, differences in race, gender, sexual orientation, gender identity or expression, political and religious affiliation, socioeconomic background, cultural background, geographic location, disabilities and abilities, relationship status, veteran status, and age. To work on diversity means that we welcome these differences, and strive to increase the visibility of traditionally underrepresented groups. Read more about our dedication to diversity and inclusion.


Does this sound interesting? If yes, let us know what you can contribute to the team. Include the title of the position you’re applying for and your name in the subject.

Proofread! Make sure you spell and capitalize WordPress and Automattic correctly. We are lucky to receive hundreds of applications for every position, so try to make your application stand out. If you apply for multiple positions or send multiple emails there will be one reply.

If you’re reading this on a site other than automattic.com please ensure you visit automattic.com/work-with-us for the latest details on applying.

Please answer the following questions in your cover letter. Applications without these questions answered will not be considered:

  1. Please tell us about a time you helped an organization navigating a major change.
  2. Are there any books you consider important to your personal growth or that you find yourself sharing with others frequently in a professional context?
  3. How much of a company’s internal playbook and training should be public to the world?
  4. What’s a question you have for us?