WordPress VIP is the enterprise division of Automattic, the company behind the open-source WordPress web-publishing platform powering 40% of the internet. We provide consulting, support, hosting, and training to some of the biggest and best WordPress sites on the web. Our clients include Facebook, Microsoft, News Corp, FiveThirtyEight, The New York Times, and many more.

The WordPress VIP division operates independently as a standalone entity, with its own executive leadership team, SaaS-based GTM strategy, and growing portfolio of solutions for the enterprise customer segment. The average enterprise customer spend is over $100K per year, and we’re rapidly scaling.

We’re looking for a Director of Enterprise Recruiting with experience in a fast-growth software environment. You’ll be a strategic partner in enabling our enterprise business to double its ARR over the course of next year. You will partner closely with business leaders to understand current and future hiring needs, and you’ll provide work direction to a high-performing team of recruiters and coordinators. 

You’ll report to Automattic’s Head of Talent Acquisition, and coordinate with the hiring leadership team in support of our five pillars of talent experience: Hiring, Onboarding, DEI, Growth and Development, and Employer Brand.

Required Experience

  • 10+ years in talent acquisition; ideally in a high-volume, high-growth environment.
  • Experience hiring GTM leaders in a high-ticket ARPU business model.
  • Experience hiring engineering, customer success, and operations management roles.
  • Proven success in managing and developing recruiting teams to deliver on aggressive hiring goals at scale.
  • Experience forecasting, setting goals & objectives, analyzing data, and measuring recruiting performance to improve effectiveness.
  • Experience building strong internal relationships with senior leadership, hiring managers, and stakeholders across multiple levels to align on business needs.
  • Experience developing innovative strategies for talent attraction.
  • Experience championing practices for diversity, equity, and inclusion across all aspects of talent experience.

Preferred Experience

  • Experience leading a distributed team, ideally in a global setting.

Key Outcomes

Within 30 days:
  • Align with finance and senior leadership strategy on projecting anticipated staffing needs. 
  • Identify key hiring metrics, and implement accurate and regular reporting to leadership.
Within 3 months:
  • Define a roadmap for the recruiting team to be a strategic partner in enabling our enterprise business to double its ARR over the course of next year.
  • Develop strategy for driving talent attraction of high-performing, world-class candidates.
Within 6 months:
  • Support the professional development of the recruiting team by providing ongoing skill-development opportunities and coaching, guided by a 6-month cadence of comprehensive individual performance and growth feedback.

The lead of this team wears a few hats:

  • Recruitment Strategy: Identify high-priority talent gaps, with an eye for building cross-functional, resilient teams that can handle any type of project thrown at them. Lead all aspects of hiring to ensure we’re attracting, hiring, and retaining the right talent. Collaborate with recruiters to improve processes and candidate experience.
  • Talent Acquisition Leadership: Coordinate with the leadership team to ensure teamwork, consistency, and shared knowledge.
  • People Management: Develop team members, guide their work and performance, and mentor their professional development. Building out the team as appropriate based on company growth and needs.
  • Strategic Leadership: Working in partnership with the leadership team to develop the strategic direction for hiring, onboarding, performance, growth, and community.

Diversity, Equity, and Inclusion

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. Read more about our dedication to diversity, equity, and inclusion and our Employee Resource Groups.


  • 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. Note: all company travel is currently optional due to COVID.
  • 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.

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. Please submit your cover letter and resume as PDFs.

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