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Director of Professional Services, WordPress VIP

Automattic· Customer Success
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Hybrid (Global (remote))$130k - $190kfull-timePosted 4mo ago

About the role

Director of Professional Services to lead and grow the Professional Services delivery organization for WordPress VIP, owning end-to-end delivery of migrations, implementations, and custom engagements for enterprise customers, while driving revenue growth and strategic direction within the Customer Experience organization.

Responsibilities

  • Build an agentic Professional Services organization—one where AI augments delivery, accelerates time-to-value, and creates capacity for higher-complexity work.
  • Build Professional Services into a growth lever: identify expansion opportunities within active engagements, and partner with Account Management and Sales to turn delivery relationships into commercial ones.
  • Lead a Professional Services team of engineers and delivery managers, delivering migrations, implementations, and custom engagements for enterprise customers.
  • Own delivery quality end-to-end: project health, escalation management, customer outcomes, and on-time, on-scope execution.
  • Build and maintain a clear menu of established service offerings, so Sales can sell them, customers can buy them, and the team can deliver them consistently.
  • Meet customers where they are. Not every engagement fits a playbook, and this role requires the judgment to scope and run custom work without losing the thread back to repeatable delivery.
  • Help set the strategic direction for Professional Services as part of the Customer Experience Senior Leadership Team, and translate it into an operating plan that the team can execute.
  • Help differentiate WordPress VIP’s services offering in the market: define what makes Professional Services at WordPress VIP distinct from what a customer could get elsewhere, and build the proof points behind it.
  • Partner with Sales & Accounts to scope and price engagements accurately, and own the hand-off from close to delivery.
  • Partner with Product, Support, and Account Management on feedback loops that continually improve WordPress VIP’s platform and services.
  • Represent Professional Services credibly with senior internal and external stakeholders, including customer executives, on complex or at-risk engagements.

Qualifications

  • 8+ years of leadership experience in Professional Services, implementation, or technical consulting. Direct experience leading a Professional Services or delivery organization is required.
  • 5+ years delivering services for enterprise SaaS or PaaS customers, ideally involving large-scale migrations or custom development.
  • Experience building a services portfolio—defining offerings, pricing them, and making them repeatable without killing the flexibility that enterprise customers need.
  • Experience working the full commercial loop—not just delivery, but scoping with Sales, pricing engagements, identifying expansion, and tying Professional Services outcomes to retention and revenue.
  • Comfortable operating in or alongside an AI-augmented delivery model.
  • Demonstrated ability to engage with executive stakeholders, both internal and external.
  • Proven track record of performance management within a team, working closely with individual contributors, leads, and HR partners.

Skills

Required:Leadership in Professional ServicesEnterprise SaaS / PaaS deliveryCommercial acumen

Benefits

  • See Benefits Page for full list of country-specific benefits.
Last updated Oct 22, 2026. Interested? Apply on the company site.

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