Director of SaaS Customer Support Operations & Automation

Entrepreneur Cooperative•, PA

9d•Remote

About The Position

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. 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.

Requirements

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.

Nice To Haves

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.

Responsibilities

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.