[Hiring] Head of Technical Support (AI & Operations) @Entrepreneur Cooperative

Role Description

We are seeking a transformational and highly technical Head of Technical Support (AI & Operations) to lead and scale a complex customer support organization supporting mission-critical software products. This is not a maintenance role. We are looking for a hands-on leader with a strong bias for action, operational excellence, and a proven ability to rebuild and optimize support functions at scale.

The ideal candidate brings deep experience managing technical support organizations, driving AI and automation initiatives, collaborating closely with Product and Engineering teams, and building operational frameworks that improve customer experience while increasing efficiency.

You will lead a team of approximately 11 professionals, including 3 support managers and 8–9 support specialists.

What You’ll Own

• Team Leadership & Operations
  • Lead, mentor, and develop support managers and support specialists
  • Own the full customer support function, including:
    • Team management
    • Hiring and performance management
    • Operational workflows
    • Team culture and accountability
  • Drive organizational and operational change management initiatives
  • Improve support processes, tooling, escalation paths, and customer workflows
• AI & Automation Strategy
  • Lead AI adoption and automation initiatives across the support organization
  • Optimize and expand Intercom AI capabilities and automation workflows
  • Build scalable ticket deflection and self-service strategies
  • Automate repetitive workflows from triage through resolution
  • Design escalation and severity frameworks within automated support environments
  • Demonstrate measurable operational improvements through automation initiatives
• Metrics, Reporting & Operational Excellence
  • Define operational KPIs and service standards for the support organization
  • Own support performance metrics including:
    • CSAT
    • Resolution times
    • Deflection rates
    • SLA performance
    • Ticket volume trends
  • Build reporting frameworks that generate actionable insights for Product, Engineering, and Leadership teams
  • Translate support data into operational and product improvement initiatives
• Technical Collaboration
  • Serve as the bridge between Support, Product, and Engineering teams
  • Represent customer technical issues with clarity, accuracy, and appropriate severity
  • Participate in technical discussions with Product Managers and Engineers
  • Help prioritize customer-impacting issues and operational improvements

Qualifications

• 10+ years of experience in customer support operations
• Significant experience in senior leadership roles owning support organizations end-to-end
• Previous experience managing managers and large support teams
• Prior experience working with complex, mission-critical software products
• Hands-on experience with Intercom and support automation tools
• Proven experience implementing AI and automation within support environments
• Strong understanding of operational KPIs and support performance frameworks
• Demonstrated success improving support efficiency, scalability, and customer experience
• Excellent analytical, communication, and leadership skills
• Strong technical fluency with the ability to collaborate effectively with Product and Engineering teams

Preferred Qualifications

• Experience building support operations in high-growth SaaS or technology companies
• Experience leading large-scale support transformation initiatives
• Background in workflow automation, AI-driven support, or conversational AI
• Strong understanding of escalation management and incident severity frameworks

What We’re Looking For

• Transformational leader with strong ownership mentality
• Highly execution-oriented with a bias for action
• Strong operational and strategic thinking capabilities
• Technical credibility with cross-functional teams
• Metrics-driven mindset focused on measurable outcomes
• Ability to thrive in fast-paced, high-growth environments

Benefits

• Opportunity to rebuild and scale a critical support organization
• High visibility and direct collaboration with Product and Engineering leadership
• Strategic influence on customer experience and operational excellence
• Ability to implement modern AI and automation strategies at scale
• Work in a fast-moving environment where support is viewed as a strategic function, not a cost center

Important Notes

• This role requires strong technical communication and operational leadership experience
• Candidates should be prepared to discuss previous automation and AI implementations in detail
• Experience supporting technically complex products is essential