Director of Professional Services, WordPress VIP

Accountabilities: Lead and manage a Professional Services organization comprising engineers and delivery managers, overseeing migrations, implementations, and custom enterprise engagements. Own end-to-end delivery performance, including project health, escalations, customer outcomes, quality, timelines, scope, and operational execution. Build an AI-augmented delivery organization that uses AI to accelerate execution, improve time-to-value, increase efficiency, and create capacity for more complex work. Develop and maintain a clear portfolio of Professional Services offerings that can be consistently scoped, priced, sold, and delivered while retaining appropriate flexibility for enterprise customers. Own the commercial performance of Professional Services, including revenue, margin, engagement pricing, expansion opportunities, and the connection between delivery outcomes, retention, and growth. Partner with Sales and Account Management to scope and price engagements accurately, manage the transition from sales to delivery, and identify opportunities to expand customer relationships. Establish and execute the strategic direction and operating plan for Professional Services as part of the broader Customer Experience leadership team. Differentiate the services portfolio in the market by defining its unique value proposition and developing evidence of customer and business impact. Collaborate with Product, Support, and Account Management to establish feedback loops that improve both services and the underlying platform. Represent Professional Services with senior internal and external stakeholders, including executive customer contacts, particularly during complex or at-risk engagements. Coach and develop delivery professionals into stronger practitioners and delivery leaders through clear expectations, direct feedback, performance management, and hands-on leadership. Requirements 8+ years of leadership experience in Professional Services, implementation, technical consulting, or a related delivery function, including direct leadership of a Professional Services or delivery organization. 5+ years delivering services for enterprise SaaS or PaaS customers, ideally involving large-scale migrations, implementations, or custom development. Proven experience building and managing a services portfolio, including defining offerings, establishing pricing, creating repeatable delivery models, and balancing standardization with customer-specific requirements. Demonstrated commercial ownership beyond delivery, including experience partnering with Sales on scoping and pricing, identifying expansion opportunities, and connecting services performance to revenue, retention, and margin. Strong understanding of AI-augmented delivery models, with practical experience using AI to improve operational workflows, delivery efficiency, and team capacity. Demonstrated ability to work effectively with executive-level internal and external stakeholders and communicate complex issues clearly and persuasively. Proven people leadership and performance-management experience, including coaching individual contributors, delivery leads, and managers in partnership with HR. An operator-first mindset with the ability to move between strategic planning and detailed delivery challenges. Strong commercial judgment, with the ability to understand and communicate revenue and margin performance alongside customer and operational outcomes. Excellent written and verbal communication skills, particularly when scoping complex engagements, managing escalations, and influencing senior stakeholders. A coaching-oriented leadership style that develops practitioners into confident delivery leaders while providing direct, constructive feedback when engagements or performance require intervention. Strategic thinking combined with strong execution skills, adaptability, and comfort operating in a fast-changing, distributed environment. Benefits Salary: $130,000–$190,000 USD, with compensation paid in local currency and the potential for higher compensation based on exceptional contribution and impact. Fully remote: Work remotely as part of a globally distributed organization. Flexible time off: Open vacation policy designed to support sustainable performance and time away from work. Competitive benefits: Access to a country-specific benefits package designed to support employees wherever they are based. Inclusive workplace: Commitment to equal opportunity, accessibility, diversity, and an inclusive employee experience. Global collaboration: Work alongside a distributed team spanning many countries, cultures, and professional backgrounds. AI-enabled work environment: Opportunity to help shape how AI is incorporated into professional services delivery and everyday workflows. High autonomy: Significant ownership and responsibility, with the freedom to drive outcomes and influence organizational strategy.