Jobgether
Director of Professional Services, WordPress VIP
Get notified of more jobs like this · No spam, ever
How your CV stacks up
Upload your CV to see how well it fits this job role
?%
Director of Professional Services, WordPress VIP
Overview
This is a senior leadership opportunity for an experienced Professional Services executive to shape and scale an enterprise delivery organization. You’ll lead teams responsible for migrations, implementations, and complex custom engagements for major enterprise customers. The role combines operational leadership with commercial ownership, including revenue, margin, pricing, and expansion opportunities. You’ll define repeatable service offerings while retaining the flexibility required for sophisticated customer environments. AI will be central to modernizing delivery, improving efficiency, and creating capacity for higher-value work. You’ll also influence broader Customer Experience strategy and collaborate closely with Sales, Product, Support, and Account Management. This is a high-autonomy, fully remote role suited to an operator who thrives on accountability, transformation, and measurable customer impact.
Responsibilities
- 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.
Reasons to use Rodeo
Start with a chat, not a search bar
Grad scheme, placement, apprenticeship? Not sure what you want yet — that's fine. Your agent talks it through with you and turns "I have no idea" into a shortlist.
It searches the market for you
Every day your agent scans the market matching roles against what actually matters to you, not just keywords on a CV.
Only hits
No noise. No "maybe this fits." Just roles with a clear explanation of why they're right — and where to focus when applying.
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.
Get help with your application
Your very own career expert that helps elevate your application to the next level.
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.
How Jobgether Works
We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team. We appreciate your interest and wish you the best!
Why Apply Through Jobgether?
Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.
“It took my CV and asked me questions relevant to understanding what kind of jobs to suggest for me. Suggestions were almost perfect. Jobs were exactly what I’ve been looking for.”
Jessica, London
Location