Director of SaaS Customer Support Operations & Automation in at The Entrepreneur Cooperative

★ PLEASE SUBMIT YOUR CV IN ENGLISH ★

Location: Remote
Employment Type: Full-Time | Independent Contractor
Please submit your CV in English

A fast-growing B2G SaaS company is helping modernize public transportation through an AI-native transit operations platform. Its cloud-based software enables transit agencies to manage and optimize services such as microtransit, paratransit, fixed-route operations, dispatching, bookings, routing, fleet coordination, and rider experiences.

About the Role

We are seeking a highly experienced Director of SaaS Customer Support Operations & Automation to lead, rebuild, and scale a customer support organization supporting complex, mission-critical SaaS products.

This role is specifically focused on supporting SaaS customers who pay for and actively use a software product. It is not focused on IT delivery, implementation, migration, infrastructure, or managed services projects.

The ideal candidate has deep experience leading customer-facing support teams in a SaaS environment, managing support managers and specialists, improving support operations through data and process optimization, and implementing automation and AI-driven support workflows.

This is a hands-on leadership role for someone who can step into a complex support environment, assess what is working, identify gaps, rebuild operational frameworks, and create measurable improvements in customer experience, team performance, efficiency, and scalability.

You will lead a team of approximately 11 professionals, including 3 support managers and 8–9 support specialists, while working closely with Product, Engineering, and Leadership teams.

• Own the end-to-end customer support function for a complex SaaS product.
• Lead, mentor, and develop support managers and support specialists.
• Manage team structure, hiring, performance management, coaching, accountability, and team culture.
• Build a high-performing support organization focused on customer outcomes, speed, quality, and scalability.
• Drive operational change management across people, processes, tools, and workflows.
• Ensure the support team is equipped to handle technical customer issues, escalations, and product-related inquiries effectively.

• Evaluate and improve current support processes, workflows, escalation paths, and operating standards.
• Create scalable systems for ticket handling, prioritization, severity management, and customer communication.
• Build repeatable support frameworks that improve resolution quality and reduce unnecessary manual work.
• Identify operational bottlenecks and implement practical solutions to improve efficiency and consistency.
• Develop support playbooks, documentation standards, and internal operating procedures.
• Ensure support processes are designed for scale, not short-term fixes.

• Lead automation and AI adoption across the support organization.
• Optimize and expand Intercom AI capabilities and automated support workflows.
• Build scalable ticket deflection and self-service strategies.
• Automate repetitive workflows across triage, routing, escalation, follow-up, and resolution.
• Use AI and automation to reduce manual workload while improving customer experience.
• Identify opportunities to improve knowledge base quality, customer self-service, and support team productivity.
• Demonstrate measurable improvements through automation, such as reduced ticket volume, faster resolution times, improved deflection rates, or improved SLA performance.

• Define and own operational KPIs and service standards for the support organization.
• Track and improve key support metrics, including:
  • CSAT
  • SLA performance
  • Resolution time
  • First response time
  • Ticket volume trends
  • Deflection rates
  • Escalation volume
  • Backlog health
  • Quality of resolution
• Build reporting frameworks that provide actionable insights for Support, Product, Engineering, and Leadership teams.
• Use support data to identify recurring issues, product gaps, workflow inefficiencies, and customer pain points.
• Translate support trends into operational and product improvement recommendations.

• Serve as the bridge between Support, Product, and Engineering teams.
• Represent customer technical issues with clarity, accuracy, and appropriate severity.
• Partner with Product and Engineering to prioritize bugs, product improvements, escalations, and recurring customer issues.
• Participate in technical discussions related to product behavior, customer-impacting issues, and supportability.
• Ensure support insights are used to improve the product and reduce future customer friction.

• 10+ years of experience in customer support, technical support, support operations, or customer experience operations.
• Significant leadership experience owning customer-facing support organizations end-to-end.
• Previous experience managing managers and support specialists.
• Direct experience supporting SaaS customers who pay for and actively use a software product.
• Strong experience with complex, technical, or mission-critical SaaS products.
• Proven experience improving support processes, workflows, escalation paths, and operational systems.
• Strong experience using data and metrics to improve support performance.
• Hands-on experience with Intercom or similar customer support platforms.
• Proven experience implementing automation, AI, self-service, or workflow optimization within a support environment.
• Strong understanding of support KPIs, including CSAT, SLA performance, resolution time, deflection rates, ticket volume, and backlog management.
• Excellent communication skills with the ability to collaborate effectively with Product, Engineering, and Leadership teams.
• Strong technical fluency and ability to understand complex product issues.
• Highly analytical, execution-oriented, and comfortable leading change in a fast-paced environment.

• Experience leading customer support for a SaaS product, not only IT services, consulting, implementation, migration, or delivery projects.
• Experience managing people, ideally including support managers or team leads.
• Experience improving support operations through process improvement, data, automation, AI, or self-service initiatives.
• Experience working closely with Product and Engineering on customer-impacting technical issues.
• Experience building scalable support processes, not just maintaining existing workflows.

This role is not a fit for candidates whose experience is primarily in:

• IT delivery projects.
• Software implementation projects.
• Migration projects.
• Infrastructure or field services support.
• Internal IT help desk operations only.
• Technical project management without SaaS customer support ownership.
• AI engineering or automation development without customer support leadership.
• Customer success without direct support operations ownership.
• Individual contributor support roles without management experience.

• Experience building or rebuilding support operations in a high-growth SaaS or technology company.
• Experience leading support transformation initiatives.
• Experience with Intercom AI, conversational AI, workflow automation, or AI-driven support tools.
• Experience creating or scaling knowledge bases, self-service resources, and ticket deflection strategies.
• Strong background in escalation management and incident severity frameworks.
• Experience supporting enterprise or mission-critical SaaS customers.
• Experience creating dashboards, reporting systems, or operational scorecards for support leadership.

• A transformational support leader with strong ownership mentality.
• A hands-on operator who can diagnose problems and implement practical solutions.
• A metrics-driven leader who uses data to improve performance.
• Someone who understands SaaS customer support deeply and can distinguish support operations from project delivery.
• A strong people leader who can coach managers, develop specialists, and create accountability.
• A process builder who can create scalable frameworks, not just react to daily issues.
• A technically credible partner to Product and Engineering.
• A leader who can use automation and AI to make support more efficient, scalable, and customer-focused.