Director, Enterprise Services & AI-Driven Delivery

Automattic Careers; United States; Remote; USD 130,000 - 190,000; Full time

Job summary

Automattic is hiring a Director of Professional Services to lead our delivery organization for migrations, implementations, and custom engagements with enterprise WordPress deployments. You’ll own the commercial result, shaping a growth-focused, AI-enabled delivery model and a repeatable service portfolio.

You will report to the VP of Customer Experience and drive end-to-end delivery quality, including scoping, pricing, and hand-off to delivery.

Qualifications

• 8+ years leading Professional Services, implementation, or technical consulting.
• 5+ years delivering services for enterprise SaaS or PaaS customers.
• Experience building a services portfolio—defining offerings, pricing them, and making them repeatable.
• Experience linking Professional Services outcomes to retention and revenue.
• Comfortable operating in an AI-augmented delivery model.
• Demonstrated ability to engage with executive stakeholders, both internal and external.
• Proven track record of performance management within a team.

Responsibilities

• Build an agentic Professional Services organization—AI-augments delivery and accelerates time-to-value.
• Grow Professional Services into a growth lever with expansion opportunities and cross-sell with Sales.
• Lead a Professional Services team delivering migrations, implementations, and custom engagements for enterprise customers.
• Own delivery quality end-to-end: health, escalation management, customer outcomes, on-time and in-scope execution.
• Build and maintain a clear menu of established service offerings for Sales and customers.
• Meet customers where they are and scope custom work without losing the thread to repeatable delivery.
• Help set the strategic direction for Professional Services as part of the CX Senior Leadership Team.
• Differentiate WordPress VIP’s services offering with compelling proof points.
• Partner with Sales & Accounts to scope and price engagements, and hand off from close to delivery.
• Collaborate with Product, Support, and Account Management on feedback loops to improve platform and services.
• Represent Professional Services credibly with senior internal and external stakeholders on complex engagements.

Skills

Leadership

Executive stakeholder engagement

Performance management

Strategic thinking

Delivery leadership

Job description

Automattic is hiring a Director of Professional Services to lead our delivery organization for migrations, implementations, and custom engagements with enterprise WordPress deployments. You’ll own the commercial result, shaping a growth-focused, AI-enabled delivery model and a repeatable service portfolio.

You will report to the VP of Customer Experience and drive end-to-end delivery quality, including scoping, pricing, and hand-off to delivery.