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Learning and Development Specialist

Automattic, the company behind, Tumblr, Jetpack, WooCommerce, and WordPress VIP is looking for an exceptional person to help us execute on the first line of our creed, “I will never stop learning.”

As our first Learning and Development Specialist, you will identify, design, and implement processes that help Automatticians learn the right things faster. “I will never stop learning” is the first tenant of our creed, and learning has a uniquely strong emphasis within Automattic. As such, you will have broad latitude to improve our coaching and professional development programs, influence our performance management processes, and design cultural practices and feedback loops that promote learning. You will report to our Chief Implementor of Learning and Development and work closely with them in every aspect of the role, helping to scale the Learning and Development organization.

About You

You have experience implementing processes across a diversity of teams and functions, and proactively analyzing the results via qualitative and quantitative methods to measure success. You have a natural inclination to understand and measure the impact that any program you implement has on the company as a whole, not just tactical metrics like course attendance.

You are extremely organized and detail oriented. You can take a high level strategic plan and fill out the details that it needs to be successful. You’re comfortable asking others for help when you require assistance to achieve your goals or need transparency on how a process works.

You almost always hit your deadlines, and if something out of your control prevents you from doing so, you communicate proactively so those depending on you can also adjust.

You communicate clearly and concisely through writing. The majority of our communication at Automattic happens via Slack or our internal wiki. You’re naturally curious and genuinely passionate about the prospect of having such broad influence on a company that’s building the future of work.

Responsibilities Include:

  • Implement processes and frameworks that improve performance and accountability across Automattic.
  • Drive the implementation and adoption of the Skills Matrices Automatticians use to plan and track their professional development.
  • Design guidelines and coordinate internal partners to build and run Learning and Development initiatives.
  • Design qualitative and quantitative surveys to measure the impact of initiatives and critically analyze the results.
  • Identify feedback loops that show Automatticians where they are effective and where they can improve.
  • Maintain an assessment program that measures the success of our 20+ executive coaches.
  • Evaluate the ROI of Learning and Development initiatives and programs.


  • 5+ years of experience with a focus on program management, performance management, change management or program assessment.
  • Strong analytical skills.
  • Highly organized, self-​motivated and able to work with significant autonomy.
  • Strong written communication skills.
  • A passion and personal interest in learning and optimization.

Diversity & Inclusion at Automattic

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.

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