Director of Professional Services

About WordPress VIP

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

About the Role

We are seeking a Director of Professional Services to lead our Professional Services delivery organization. You will oversee the day-to-day operations of a team responsible for migrations, implementations, and custom engagements for complex enterprise WordPress deployments. Reporting to the VP of Customer Experience (CX), you will be a key member of the CX Senior Leadership Team. This is a revenue-generating business where you will own the commercial results, not just delivery quality. You'll be joining a team with established delivery capabilities and a strong customer base, focusing on a refined service menu, faster time-to-value, and an AI-augmented delivery model.

Responsibilities

• Build an agentic Professional Services organization where AI augments delivery, accelerates time-to-value, and creates capacity for higher-complexity work.
• Drive Professional Services as a growth lever by identifying expansion opportunities and partnering with Account Management and Sales.
• Lead a team of engineers and delivery managers in 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.
• Develop and maintain a clear menu of established service offerings for consistent sales and delivery.
• Scope and manage custom work with judgment, ensuring it aligns with repeatable delivery models.
• Contribute to setting the strategic direction for Professional Services as part of the Customer Experience Senior Leadership Team and translate it into an actionable operating plan.
• Differentiate WordPress VIP’s services offering by defining unique value propositions and building supporting proof points.
• Partner with Sales & Accounts to accurately scope and price engagements and manage the hand-off from close to delivery.
• Collaborate with Product, Support, and Account Management on feedback loops to improve the platform and services.
• Represent Professional Services credibly with senior internal and external stakeholders 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, including defining offerings, pricing, and ensuring repeatability while maintaining flexibility.
• Experience managing the full commercial loop: scoping with Sales, pricing, identifying expansion opportunities, and linking Professional Services outcomes to retention and revenue.
• Genuine fluency with AI-augmented delivery models and how AI impacts work.
• Demonstrated ability to engage with executive stakeholders, both internal and external.
• Proven track record of performance management within a team, collaborating with individual contributors, leads, and HR partners.

How You Work

• Operator First: You hold strategy while attending to delivery details; action-oriented.
• Commercially Accountable: You view Professional Services as a business, understanding and articulating revenue and margin.
• Strong, Persuasive Communicator: Capable of scoping complex engagements, writing clearly under pressure, and holding executive attention.
• Coach, Not Just a Manager: Develops practitioners into leads, provides direct feedback, and guides execution.
• Strategic and Grounded: Can set strategic direction and provide granular project guidance.

Compensation and Benefits

• Salary Range: $130,000 - $190,000 USD (global range, paid in local currency).
• Pay will reflect potential contribution and impact, potentially exceeding the stated range.
• Straightforward, competitive base salary with no complex variable components.
• Fully-remote company with an open vacation policy.
• Comprehensive benefits package (details available on the Benefits Page).

About Automattic

Now in our 20th year, Automattic is the company behind WordPress.com, WooCommerce, Beeper, Tumblr, and more. We are dedicated to making the web a better place.

We are a distributed company with over 1500 Automatticians globally, united by a mission to democratize publishing, commerce, and messaging. We champion Open Source, with most of our work available under the GPL. Automattic is a Most Loved Company, an Equal Opportunity employer, and Disability Confident Committed. We are committed to an accessible hiring process and support Employee Resource Groups.