Director of Professional Services, WordPress VIP

This is a senior leadership opportunity for an experienced Professional Services executive to shape and scale an enterprise delivery organization. You’ll lead teams responsible for migrations, implementations, and complex custom engagements for major enterprise customers. The role combines operational leadership with commercial ownership, including revenue, margin, pricing, and expansion opportunities. You’ll define repeatable service offerings while retaining the flexibility required for sophisticated customer environments. AI will be central to modernizing delivery, improving efficiency, and creating capacity for higher-value work. You’ll also influence broader Customer Experience strategy and collaborate closely with Sales, Product, Support, and Account Management. This is a high-autonomy, fully remote role suited to an operator who thrives on accountability, transformation, and measurable customer impact.

Accountabilities

• Lead and manage a Professional Services organization comprising engineers and delivery managers, overseeing migrations, implementations, and custom enterprise engagements.
• Own end-to-end delivery performance, including project health, escalations, customer outcomes, quality, timelines, scope, and operational execution.
• Build an AI-augmented delivery organization that uses AI to accelerate execution, improve time-to-value, increase efficiency, and create capacity for more complex work.
• Develop and maintain a clear portfolio of Professional Services offerings that can be consistently scoped, priced, sold, and delivered while retaining appropriate flexibility for enterprise customers.
• Own the commercial performance of Professional Services, including revenue, margin, engagement pricing, expansion opportunities, and the connection between delivery outcomes, retention, and growth.
• Partner with Sales and Account Management to scope and price engagements accurately, manage the transition from sales to delivery, and identify opportunities to expand customer relationships.
• Establish and execute the strategic direction and operating plan for Professional Services as part of the broader Customer Experience leadership team.
• Differentiate the services portfolio in the market by defining its unique value proposition and developing evidence of customer and business impact.
• Collaborate with Product, Support, and Account Management to establish feedback loops that improve both services and the underlying platform.
• Represent Professional Services with senior internal and external stakeholders, including executive customer contacts, particularly during complex or at-risk engagements.
• Coach and develop delivery professionals into stronger practitioners and delivery leaders through clear expectations, direct feedback, performance management, and hands-on leadership.