Would you like to take part in building the future of our distributed workforce? Automattic is a place like no other: our fast-growing team of 1,700+ works from home (or any other location they choose), in one of 89+ countries, to democratize publishing and make the web a better place. Check out our Work With Us page for more info on how we work, our development process, and benefits.

The Human League (externally known as HR) team’s goal is to ensure our company is the best place Automatticians have ever worked, making each person feel welcomed, included, valued, and respected. Our mission is to be leaders by building and supporting a globally distributed, diverse, authentic and inclusive workforce, where Automatticians can thrive. We need a Benefits Wrangler to join our team and help scale our distributed model as we grow.

The Benefits Wrangler will be a strategic partner to Automatticians and the Human League team, and be responsible for coordinating all benefits and retirement programs in the US, Canada, Australia, the UK, Ireland, and South Africa. You will maintain vendor relationships in each country, and coordinate all US benefits and retirement programs, including medical, dental, vision, life insurance, short and long-term disability, and 401(k) plan.

Do you have:

  • Experience working with distributed team members?
  • Experience leading all aspects of benefits strategy, design, administration, and compliance for a global company?
  • Experience developing, implementing, and maintaining US benefits programs, including group medical, dental, vision insurance, life and accident, disability, health saving accounts, etc.?
  • Experience in handling compliance with ERISA, COBRA, HIPAA, Section 125, HSA rules, and other benefit and regulatory requirements globally?
  • Experience in developing benefits communications and counseling employees on benefits-related issues?
  • Experience in coordinating vendor relationships and supervising vendor performance?
  • 6+ years proven experience working in a similar position?
  • A passion for elegant, simple, automated solutions that keep operations running efficiently?
  • A love for working in dynamic and fast-paced environments?
  • An ability to see opportunities to make the work environment better and the initiative to move forward with action?
  • Desire to learn and experiment with new processes and technologies?
  • The ability to accept and respond constructively to feedback?
  • Outstanding verbal and written communication skills in English?
  • Experience using WordPress (most of our systems are based on WordPress)?

We are looking to expand our team and strive to reflect the diversity of Automatticians currently working with us. We value diversity and know that different perspectives will ensure our team is innovative and creative-thinking.


Does this sound exciting? If yes, click the Apply button below and fill out our application form. In your cover letter, let us know what you can contribute to the team. You will need to attach a cover letter and résumé. Proofread! Make sure you spell and capitalize WordPress and Automattic correctly. We are lucky to receive many applications, so make yours stand out.

Please answer the following questions in your cover letter (applications without this information will not be reviewed):

  • What’s your favorite HR tool and why?
  • Tell us about an exciting situation you were involved in while managing benefits. What made it exciting to you? How was it resolved?
  • In one paragraph, describe the qualities that you admire in the best benefits professional you've worked with.

We look forward to hearing from you!


About Automattic

We are the people behind WordPress.com, WooCommerce, Jetpack, Tumblr, Simplenote, Longreads, Day One, and more. We believe in making the web a better place.

We’re a distributed company with more than 1800 Automatticians in 90+ 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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