Director of Professional Services, WordPress VIP

About this role

Lead WordPress VIP’s Professional Services organization, delivering enterprise migrations, implementations, and custom engagements. Own delivery quality and commercial performance while developing repeatable services and using AI to improve capacity and time-to-value.

About the company

Automattic builds WordPress.com, WooCommerce, Tumblr, and related products that power publishing and ecommerce on the open web.

The team

Professional Services organization; reports to the VP of Customer Experience and is part of the CX Senior Leadership Team.

What you'll do

• Lead engineers and delivery managers across enterprise migrations, implementations, and custom engagements
• Own project health, escalations, customer outcomes, and on-time, on-scope delivery
• Develop a clear, repeatable services portfolio while accommodating custom customer needs
• Drive revenue growth through expansion opportunities and partnership with Sales and Account Management
• Scope and price engagements, and manage handoffs from sales close to delivery
• Build an AI-augmented delivery organization
• Set Professional Services strategy and operating plans with CX leadership
• Partner with Product, Support, and Account Management on improvement feedback loops

What we're looking for

• 8+ years of leadership experience in Professional Services, implementation, or technical consulting, including direct leadership of a delivery organization
• 5+ years delivering services for enterprise SaaS or PaaS customers
• Experience defining, pricing, and scaling a services portfolio
• Experience with the full commercial cycle, including scoping, pricing, expansion, and revenue outcomes
• Fluency with AI-augmented delivery models
• Executive stakeholder engagement and team performance-management experience

Nice to have

• Experience with large-scale migrations or custom development

Benefits

• Open vacation policy
• Fully remote work