Director of Professional Services, WordPress VIP

About the role

This senior leadership position will shape and scale an enterprise delivery organization for WordPress VIP, overseeing migrations, implementations, and complex custom engagements for major enterprise customers. The role combines operational leadership with commercial ownership, leveraging AI to modernize delivery.

Key responsibilities

• Lead and manage a Professional Services organization of engineers and delivery managers, ensuring project health, quality, timelines, and scope.
• Build an AI‑augmented delivery model to accelerate execution, improve time‑to‑value, and increase efficiency.
• Develop and maintain a clear portfolio of repeatable service offerings while retaining flexibility for enterprise needs.
• Own commercial performance, including revenue, margin, pricing, and expansion opportunities.
• Partner with Sales, Product, Support, and Account Management to scope, price, and transition engagements.

Required profile

• 8+ years of leadership experience in Professional Services, implementation, or technical consulting, with direct management of a delivery organization.
• 5+ years delivering services for enterprise SaaS or PaaS customers, including large‑scale migrations and custom development.
• Proven commercial ownership experience, collaborating with Sales on scoping, pricing, and expansion.
• Strong ability to work with executive‑level stakeholders and communicate complex issues persuasively.

Required skills

• Experience building and managing a services portfolio with defined offerings and pricing.
• Practical knowledge of AI‑augmented delivery models and using AI to improve operational workflows.

What we offer

• Salary range $130,000–$190,000 USD, paid in local currency with potential for higher compensation.
• Fully remote work with flexible time‑off and open vacation policy.
• Country‑specific benefits package and inclusive workplace commitment.
• Opportunity to shape AI integration in professional services delivery.