Head of Support

About OnTheGoSystems

OnTheGoSystems is a profitable $12M fully remote company behind WPML, one of the most popular WordPress plugins in the world, serving over 250,000 customers globally. We’re looking for a Head of Support to own and continuously improve the entire support experience across our products. This role sits at the intersection of product, engineering, and customer success. You will drive a modern support operation that combines AI-powered, human, and developer-led VIP support, ensuring that every client interaction reflects the quality of our products.

What You’ll Do

• Lead our global support organization, including a human support team, AI-powered support systems, and developer-led VIP support.
• Own the support strategy, performance metrics, and operational standards for the entire support organization.
• Continuously improve support quality using data by reviewing tickets, measuring customer satisfaction, and identifying recurring issues and key client pain points.
• Work closely with development teams to turn recurring support problems into product improvements, reducing future support demand.
• Collaborate with the AI team to expand automation and strengthen the knowledge base that powers our AI support.
• Act as the final escalation point for complex or sensitive client situations.

Indicators You’re a Good Fit

• You have experience in PHP, JavaScript, CSS, and HTML, allowing you to follow technical discussions and step into complex escalations when needed.
• You’re comfortable working with WordPress and debugging issues.
• You are skilled in modern AI technologies and know how to apply them to real support workflows.
• You have experience leading and scaling support or customer-facing teams while maintaining high-quality standards.
• You’ve worked directly with clients and can handle complex or sensitive situations calmly and professionally.
• You’ve built or delivered products, understanding engineering trade-offs and practical constraints.
• You have a data-driven mindset, using metrics such as resolution time, automation rate, and customer satisfaction to identify root causes and drive continuous improvement.

If you want to play a key role in shaping support for hundreds of thousands of users and contribute to a modern system where people and AI work together, we’d love to hear from you. Apply today to join OnTheGoSystems! To ensure a fair and equitable process, only applications submitted through our official application form will be considered. Due to the high volume of applications, we will only be able to contact candidates selected to move forward in the interview process. We sincerely appreciate your interest and the time you invest in applying.

Key skills/competency

• Head of Support
• Customer Support Leadership
• AI in Support
• WordPress Expertise
• Technical Support
• Customer Success
• Team Management
• Data Analysis
• Problem Solving
• Escalation Management