Director of Customer Success Operations

WordPress VIP is the leading provider of enterprise WordPress, trusted by brands like CNN, Facebook, and Microsoft. We’re looking for an experienced leader to direct the operations of VIP’s Customer Success organization. We offer flexible, remote work arrangements allowing our team members to work when and where they feel best.

In this role, you’ll work directly with VIP’s Chief Customer Officer to drive platform adoption, renewal, and success with our Enterprise customers. You’ll be responsible for helping a 24/7 operation with ~90 support engineers, software engineers, technical account managers, and relationship managers run efficiently and effectively. You’ll be looking for ways to invest in our team to help us drive value for our customers. Most of all, you’ll ensure that we’re providing a consistent, responsive, high-quality experience for all of our customers.


  • Lead an operations group supporting a global customer success team.
  • Drive critical initiatives in partnership with VIP’s Chief Customer Officer. 
  • Report, analyze, and action on data around customer renewals, customer journeys, upsells, and churn.
  • Define and report on key metrics that evaluate support’s efficiency and performance.
  • Develop reporting to amplify the voice of the customer across the business (ex. product, marketing).
  • Develop processes for customer concerns, incident management, and on-call.
  • Build internal pathways for customer success professional development.
  • Own and improve customer success tooling (ex. Gainsight, Zendesk) and team workflows for efficiency and consistency.
  • Forecast staffing demand, drive scheduling, and maintain 24/7 coverage.

We are looking for an applicant with experience serving a high-complexity product for large, global enterprises. Proficiency with WordPress is nice to have, though not required. Bonus points if you have experience working on a distributed team.

As a part of our globally distributed team you can live anywhere in the world. Effectiveness in this role will mean occasionally shifting hours across weekends and odd hours to best coordinate with our distributed team.

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 suspended 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.

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