Director of Professional Services, WordPress VIP

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.

Experience

• 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. What we need is genuine fluency with how AI changes the work—not just awareness that it exists.
• Demonstrated ability to communicate effectively across teams and with executive stakeholders.