Director of Professional Services, WordPress VIP

About the role

This senior leadership role leads a Professional Services organization for WordPress VIP, overseeing migrations, implementations and complex custom engagements for enterprise customers. The position is fully remote, based in Bulgaria, and combines operational leadership with commercial ownership.

Key responsibilities

• Lead and manage engineers and delivery managers delivering migrations, implementations and custom enterprise engagements.
• Own end‑to‑end delivery performance, including project health, escalations, timelines, scope and quality.
• Build an AI‑augmented delivery organization to accelerate execution and increase efficiency.
• Develop and maintain a clear portfolio of repeatable Professional Services offerings.
• Own commercial performance – revenue, margin, pricing and expansion opportunities.
• Partner with Sales and Account Management to scope, price and transition engagements.
• Define strategic direction and operating plan as part of the Customer Experience leadership team.
• Represent Professional Services with senior internal and external stakeholders.
• Coach and develop delivery professionals into stronger practitioners and leaders.

Required profile

• 8+ years of leadership experience in Professional Services, implementation or technical consulting.
• 5+ years delivering services for enterprise SaaS or PaaS customers, including large‑scale migrations.
• Proven commercial ownership and experience partnering with Sales on scoping and pricing.
• Strong understanding of AI‑augmented delivery models with practical experience.
• Excellent communication skills with executive‑level stakeholders.
• Demonstrated people leadership and performance‑management experience.

Required skills

• AI
• SaaS
• PaaS
• WordPress

What we offer

• Salary $130,000–$190,000 USD, paid in local currency with potential for higher compensation.
• Fully remote work with flexible time off and open vacation policy.
• Country‑specific competitive benefits package.
• Inclusive workplace committed to diversity and equal opportunity.
• Opportunity to shape AI‑enabled work environment and high autonomy.