Director of Professional Services, WordPress VIP

Details

WordPress VIP is hiring a Director of Professional Services to lead its Professional Services delivery organization. The role owns the day-to-day operation of a team responsible for migrations, implementations, and custom engagements for complex enterprise WordPress deployments. It reports to the VP of Customer Experience and is part of the Customer Experience Senior Leadership Team.

Professional Services is a revenue-generating business. The role is responsible for delivery quality as well as commercial performance, including service offerings, pricing, expansion opportunities, revenue, and margin.

Responsibilities

• Build an agentic Professional Services organization in which AI augments delivery, accelerates time-to-value, and creates capacity for higher-complexity work.
• Develop Professional Services as a growth lever by identifying expansion opportunities within active engagements and partnering with Account Management and Sales.
• Lead a team of engineers and delivery managers delivering migrations, implementations, and custom engagements for enterprise customers.
• Own end-to-end delivery quality, including project health, escalation management, customer outcomes, and on-time, on-scope execution.
• Build and maintain a clear, repeatable menu of service offerings that Sales can sell and customers can purchase.
• Scope and run custom engagements while maintaining a connection to repeatable delivery models.
• Help define the strategic direction of Professional Services and translate it into an executable operating plan.
• Differentiate WordPress VIP's Professional Services offering in the market and develop supporting proof points.
• Partner with Sales and Accounts to scope and price engagements accurately and manage the hand-off from close to delivery.
• Partner with Product, Support, and Account Management to create feedback loops that improve the platform and services.
• Represent Professional Services with senior internal and external stakeholders, including customer executives, on complex or at-risk engagements.

Requirements

• 8+ years of leadership experience in Professional Services, implementation, or technical consulting.
• Direct experience leading a Professional Services or delivery organization.
• 5+ years delivering services for enterprise SaaS or PaaS customers, ideally involving large-scale migrations or custom development.
• Experience building a services portfolio, including defining offerings, pricing them, and making them repeatable while retaining enterprise flexibility.
• Experience with the full commercial cycle, including sales scoping, engagement pricing, expansion identification, and connecting Professional Services outcomes to retention and revenue.
• Fluency with AI-augmented delivery models and how AI changes professional services work.
• Demonstrated ability to engage executive stakeholders internally and externally.
• Proven performance-management experience working with individual contributors, leads, and HR partners.
• Strong delivery operations, commercial accountability, communication, coaching, and strategic planning skills.

Benefits

• Salary range of $130,000–$190,000 USD, with ranges applied globally and pay provided in local currency.
• Potential compensation may exceed the stated range based on contribution and impact.
• Fully remote work.
• Open vacation policy.
• Country-specific benefits are available through Automattic's benefits program.