[Hiring] Director of Professional Services @Automattic Careers

Role Description

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.

• 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.

Qualifications

• 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. Genuine fluency with how AI changes the work.
• 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.

Requirements

• Operator first: You hold the strategy in your head and still show up for the delivery details. More do than say.
• Commercially accountable: You think about Professional Services as a business, not a function. You know your revenue number, you know your margin, and you can talk about both with the same fluency you bring to delivery.
• Strong, persuasive communicator: You can scope a hard engagement, write clearly under pressure, and hold executive attention without overstating your case.
• Coach, not just a manager: You develop practitioners into delivery leads. You give direct feedback. You’ll step in when something must be done a certain way, and you know when not to.
• Strategic and grounded: You can recommend a services portfolio direction, and also tell a project manager exactly where their engagement is going wrong.

Benefits

• Salary range: $130,000 - $190,000 USD. Please note that salary ranges are global, regardless of location, and we pay in local currency.
• We are searching for high-caliber candidates with the skills and qualities to have a net positive for Automattic. Pay will reflect the potential contribution and the impact you can bring, which may, in some cases, go beyond the range stated.
• We’re pleased to offer a straightforward, competitive base salary, providing financial clarity without complex variable components.
• This isn’t your typical work-from-home job: we are a fully-remote company with an open vacation policy.