Director, AI-Driven Enterprise Services

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

Benefits offered by this job

Fully remote

Open vacation policy

Job summary

Automattic is hiring a Director of Professional Services to lead the WordPress VIP delivery organization. You will own day-to-day operations of a team delivering migrations, implementations, and custom engagements for enterprise customers, reporting to the VP of Customer Experience.

You will drive a sharper service menu, faster time-to-value, and AI-enabled delivery. The role blends strategy, client leadership, and revenue responsibility, with a global, fully remote team and a focus on scale,

Qualifications

• 8+ years of leadership in Professional Services or delivery organizations.
• 5+ years delivering services for enterprise SaaS or PaaS customers, with large migrations or custom development.
• Experience building a services portfolio with repeatable offerings.
• Experience scoping with Sales, pricing engagements, and tying outcomes to retention and revenue.
• Comfortable operating in an AI-augmented delivery model.

Responsibilities

• Build an agentic Professional Services organization where AI augments delivery and accelerates time-to-value.
• Grow SA into a growth lever by identifying expansion opportunities within engagements and partnering with Sales to commercialize delivery relationships.
• Lead a 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, on-time and on-scope execution.
• Maintain a clear menu of service offerings for Sales to sell and customers to buy, while ensuring repeatable delivery.

Skills

Leadership

Enterprise SaaS

Migrations

Sales alignment

AI-augmented delivery

Executive stakeholder engagement

Performance management

Job description

Automattic is hiring a Director of Professional Services to lead the WordPress VIP delivery organization. You will own day-to-day operations of a team delivering migrations, implementations, and custom engagements for enterprise customers, reporting to the VP of Customer Experience.

You will drive a sharper service menu, faster time-to-value, and AI-enabled delivery. The role blends strategy, client leadership, and revenue responsibility, with a global, fully remote team and a focus on scale,