Director of Professional Services, WordPress VIP

WordPress VIP is the world’s leading enterprise content management platform. We help the world’s largest companies—including Meta, Salesforce, and Disney—create innovative digital experiences with WordPress.

We are hiring a Director of Professional Services to run our Professional Services delivery organization. You will own the day-to-day operation of a team that handles migrations, implementations, and custom engagements for some of the most complex enterprise WordPress deployments in the world. The role reports to the VP of Customer Experience (CX) as part of the CX Senior Leadership Team.

You’re walking into a team with real delivery capability and an established customer base. The work now is sharper: a tighter service menu, faster time-to-value, a delivery model that can flex to what enterprise customers actually need—and an organization that increasingly runs on AI. Professional Services at WordPress VIP is a revenue-generating business. The person in this seat owns that commercial result, not just the delivery quality behind it.

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 engage with executive stakeholders, both internal and external.
• Proven track record of performance management within a team, working closely with individual contributors, leads, and HR partners.

About Automattic

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