Director, Customer Success

About the Company and Mission

Gorgias is pioneering the future of Conversational Commerce by creating an integrated AI platform that enables brands to sell, support, and reconnect with their customers throughout the entire buying journey. Their goal is to transform every brand-customer interaction into a personalized, seamless, and intelligent relationship, enhancing ecommerce experiences with advanced AI technology.

Role Overview

The Director of Customer Success will oversee the entire post-sale relationship for Commercial and Enterprise merchants at Gorgias, concentrating on maximizing Net Revenue Retention (NRR). This leadership role involves building and evolving the Customer Success (CS) organization to leverage AI for high-volume execution while focusing human efforts on strategic judgment, relationship management, and commercial outcomes.

Key Responsibilities

• Lead and design the CS organizational structure including managing two CS Managers for Commercial and Enterprise segments and Customer Success Managers (CSMs) for key accounts.
• Directly mentor CS Managers to ensure team performance, professional growth, and achievement of goals.
• Define and implement organizational objectives and key results (OKRs) aligned with overall company strategy.
• Manage the CS budget, balancing investments in human resources and AI capabilities.
• Develop frameworks for performance management and career progression within the CS teams.
• Foster a culture of accountability, high standards, and make necessary performance-related decisions.
• Own NRR strategies tailored to Commercial and Enterprise segments and ensure account health and expansion initiatives are executed effectively.
• Engage personally with strategic accounts and handle escalated issues with senior-level judgment.
• Establish reporting and forecasting systems to monitor renewals, growth pipelines, and churn risks with transparent reporting to leadership.
• Steer executive business reviews to demonstrate return on investment and AI adoption benefits.
• Drive the transformation of Customer Success into an AI-first function by collaborating closely with Product and Engineering to refine the AI agent roadmap based on customer feedback.
• Enhance AI literacy across the CS organization to empower team members in leveraging AI tools effectively.
• Represent the CS function in company-wide AI strategy discussions, influencing product development and organizational direction.
• Partner with leadership across Sales, Implementation, and Product teams to ensure cohesive customer experiences throughout the lifecycle.
• Provide regular CS performance updates and insights to the COO and participate in leadership and board meetings.

Candidate Profile

• Over 10 years of experience in SaaS Customer Success with at least 5 years leading layered CS teams managing multiple managers.
• Demonstrated success scaling AI-enhanced Customer Success operations driven by technology rather than manpower alone.
• Strong AI-native mindset, preferring automation-first approaches and viewing AI as essential, not supplementary.
• Proven track record owning full-book commercial outcomes (NRR/GRR) with distinct strategies for Commercial and Enterprise segments.
• Experience in building or overhauling CS organizations from the ground up, comfortable navigating ambiguity and greenfield challenges.
• Ability to operate effectively with senior leadership, including budget management and performance decisions at high organizational levels.
• Skilled leader of managers, experienced in developing leadership talent and scaling organizational structures.
• Technical proficiency with AI capabilities and limitations, able to engage in product roadmap discussions confidently.
• Systems thinker who prefers structured processes and scalable solutions over ad hoc efforts.
• High standards for leadership, including readiness to make tough personnel decisions when necessary.
• Based in New York City, Toronto, or San Francisco with hybrid work expectations.

Preferred Qualifications

• Previous roles in AI-native companies or experience with AI-driven service delivery models.
• Exposure to multiple merchant segments within a single organization.
• Collaborative experience with Product teams on AI roadmap development.
• Background in ecommerce or direct-to-consumer industries.

Company Culture and Additional Information

AI is deeply integrated into everyday workflows, with team members having access to advanced AI tools and continuous learning budgets to explore new technology. The organization encourages sharing of AI discoveries and innovations to enhance creativity and customer service. Gorgias is committed to diversity, inclusion, and providing accommodations during recruitment. Compensation ranges from CA$220,815 to CA$259,915.

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