Manager, Enterprise Customer Success

About the role

You will lead the design and execution of the enterprise customer success model at Gorgias, defining what it means to deliver AI value at scale for our most strategic merchants. You will own the end-to-end outcomes, retention, and expansion of a portfolio of enterprise accounts ranging from $30K ARR to well into six figures, ensuring that AI adoption and utilization are central to the relationship. In this role, you will blend human strategic judgment with AI execution to redefine how Customer Success operates, moving from traditional support to proactive, data-driven value creation. You will be the primary owner of AI outcomes for enterprise customers, acting as the critical link between product, sales, and the merchant's business goals. You will coach a team of up to 10 Enterprise CSMs to operate with the speed and precision required in a high-growth, AI-first environment. This role requires you to build the playbook from the ground up, establishing the frameworks, rituals, and standards that make enterprise success scalable and repeatable. Based in Toronto and reporting to the Head of Customer Experience, you will shape the future of commerce by ensuring that every conversation between brand and customer delivers measurable, intelligent value.

Key facts

What you'll do

Lead, coach, and develop a team of up to 10 Enterprise CSMs through structured performance frameworks, regular 1:1s, and team rituals that reinforce accountability and growth.

Translate high-level CX strategy into clear, measurable OKRs and actionable plans that align the Enterprise team with Gorgias' enterprise growth objectives.

Own account health and Net Revenue Retention (NRR) across a portfolio of enterprise accounts, driving strategic conversations that unlock expansion and deepen adoption.

Design and guide the execution of high-impact executive business reviews (QBRs), demonstrating AI utilization, ROI, and strategic progress for each merchant.

Build and maintain deep, consultative relationships with senior stakeholders, ensuring that Gorgias remains the strategic partner of choice for each enterprise customer.

Upskill the team on emerging AI capabilities, including vibe coding, custom solution building, and AI agent management, enabling CSMs to deliver deeper value with greater efficiency.

Establish clear performance standards and drive a culture of genuine accountability, making difficult decisions when necessary to maintain a high-performing team.

Surface recurring customer challenges early and coach CSMs to resolve issues at the appropriate level, minimizing escalations and reinforcing trust.

Partner closely with Sales, Product, and Engineering to provide frontline feedback from enterprise customers, informing product roadmap decisions and go-to-market strategies.

Own the end-to-end success playbook for AI Services at Gorgias, defining processes, best practices, and templates that scale across the team.

Champion the adoption of AI agents and automation within customer workflows, ensuring merchants realize tangible efficiency and revenue outcomes.

Lead proactive health monitoring and forecasting for enterprise accounts, identifying risks and opportunities before they impact retention or growth.

Develop and maintain executive-level reporting and dashboards that communicate the value and impact of Gorgias AI to merchant leadership.

Act as the operational backbone for the Enterprise CS team, removing blockers, aligning resources, and ensuring timely, high-quality execution.

Requirements

You have operated in complex enterprise environments, managing long sales cycles and navigating senior stakeholder dynamics with confidence and credibility.

You have a proven track record of building and leading high-performing teams, with experience in coaching, performance management, and developing scalable playbooks.

You understand what it means to own outcomes end-to-end, taking full responsibility for retention, expansion, and value realization in a SaaS environment.

You are comfortable making difficult performance decisions, including addressing underperformance and managing exits when necessary to maintain team standards.

You have experience aligning AI or technology initiatives with measurable business outcomes, demonstrating how new tools create real value for customers.

You are highly analytical and data-driven, capable of translating qualitative customer insights into quantitative strategies and actions.

You communicate with precision and presence, able to convey complex concepts to both technical and non-technical audiences with clarity and confidence.

You are a builder at heart, energized by creating processes, frameworks, and systems that scale efficiently without sacrificing quality or humanity.

Nice to have

Experience working with AI agents, conversational AI platforms, or commerce technology stacks.

Background in ecommerce, retail, or D2C environments where speed and personalization are critical.

Practical notes

This role is based in Toronto.

The position reports to the Head of Customer Experience.

Employment is full_time.

Candidates must be eligible to work in Canada without sponsorship.

The role involves frequent collaboration across Sales, Product, and Engineering teams.

Strong written and verbal communication skills in English are essential.

This position requires a high degree of comfort with ambiguity and rapid iteration in a fast-growing startup environment.

You will be expected to travel occasionally for customer visits, team offsites, and industry events as needed.

The successful candidate will be required to pass standard background checks as part of the hiring process.

This role involves exposure to confidential commercial and technical information, requiring discretion and sound judgment at all times.

Performance in this role will be evaluated based on enterprise customer outcomes, retention, team development, and AI adoption metrics.

This is a hands-on leadership role that demands both strategic thinking and day-to-day execution.

You will be part of a growing team that is redefining customer success in the era of AI-driven commerce.

This role is critical to scaling Gorgias' enterprise business and ensuring that our customers derive maximum value from our platform.

You will have the opportunity to shape the future of customer success and leave a lasting impact on how AI is used to serve merchants around the world.