Automattic, the company behind, Tumblr, Jetpack, WooCommerce, and WordPress VIP is looking for a thoughtful and experienced facilitator who also has 1-on-1 coaching skills to help us execute on the first line of our creed, “I will never stop learning.”

As our second Facilitator Coach you will facilitate individual and group sessions that teach general management best practices along with Automattic-specific strategies for success. One of our Learning and Development goals at Automattic is to develop more internal coaching and facilitation capacity among our Leads, and the group sessions that you facilitate will be one of the primary methods by which we do that.

You will be the eyes and ears of Learning and Development. Through both the group sessions you facilitate and 1-on-1 coaching sessions that may accompany them, you will help us distill the common challenges Automatticians experience across the company, and design new interventions to address them. You will report to our Chief Implementer of Learning and Development and work closely with him in every aspect of the role, helping to scale the Learning and Development organization.

About you

You are a seasoned facilitator with 1-on-1 coaching as well as group facilitation experience. You have been a manager yourself in the past and ideally have experience leading product teams. You’re adept at building rapport and hold the view that people learn best when they come to the answers themselves. You have worked with other coaches in the past and can meaningfully contribute to improving the way we run our coaching program overall. Experience leading communities of practice (Masterminds, cohort-based learning, peer support groups, etc.) is a plus.

Responsibilities Include:

  • Facilitating various group sessions that focus on unique Automattic needs like having difficult conversations, giving and receiving feedback, new lead onboarding, leading through uncertainty, etc.
  • Providing 1-on-1 coaching for a subset of Automattic leaders.
  • Distilling learnings on our largest organizational challenges from your interactions with Automatticians.
  • Sourcing or publishing relevant leadership content for Automatticians.
  • Working with our Learning and Development Manager to improve the effectiveness of our coaching program.
  • Developing training modules to address additional leadership needs in conjunction with the rest of the Learning and Development Team.


  • 4+ years of experience facilitating group sessions.
  • 1-on-1 coaching experience.
  • Experience managing your own teams.
  • Exceptional written communication skills.
  • Highly organized, self-​motivated and able to work with significant autonomy.
  • A passion and personal interest in learning and optimization.
  • Availability to support Automatticians in Asia-Pacific timezones.
  • Experience working with distributed organizations is a plus but not required.

Diversity & Inclusion at Automattic

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. Learn more about our dedication to diversity and inclusion and our Employee Resource Groups.

How to apply


Does this sound interesting? If yes, fill out our application form below. In your cover letter, let us know what you can contribute to the team. Proofread! Make sure you spell and capitalize WordPress and Automattic correctly. We are lucky to receive many applications for this position, so try to make your application stand out. Please answer the following questions in your cover letter. Applications without these questions answered will not be considered:

  1. Describe how you’ve evaluated the success or failure of a group process that you’ve facilitated along with the next steps you took after the evaluation.
  2. In your experience what are the most common challenges that leaders face, and how do you address them in your sessions?
  3. Describe a process you’ve personally undertaken to learn something challenging and the outcome.
  4. What’s a question you have for us?

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