About the Team

The Enterprise Customer Success team at Gorgias works with our most strategic merchants - relationships ranging from $30K ARR up to well into six figures. As AI becomes the cornerstone of modern commerce, our Enterprise CSMs are at the forefront of helping merchants unlock the full power of Gorgias: from AI Agent configuration and optimization to custom-built automations and integrations. We move fast, think like operators, and genuinely care about the outcomes we drive for our customers.

We're a team in evolution. The next chapter of Enterprise CS at Gorgias isn't just about managing accounts; it's about redesigning how Customer Success works: blending AI agents and human judgment to deliver a new tier of speed, depth, and impact. This role is central to that mission.

This isn't a traditional Customer Success role. It's the person who owns AI value delivery at scale; the way Sales owns revenue, this team owns AI outcomes. We're building the model from scratch, and this leader is the one driving it.

We're also moving upmarket. That means we need an enterprise leader in the truest sense - someone who has operated inside complex enterprise environments, understands long sales cycles and senior stakeholder dynamics, and can coach a team to show up with the credibility, polish, and strategic depth that enterprise customers expect. This isn't a role for someone who is enterprise-curious. It's for someone who has lived it.

About the Role

As Senior Manager of Enterprise Customer Success, you'll lead a team of up to 10 Enterprise CSMs and own the outcomes, retention, and growth of Gorgias's most strategic merchant relationships. This is not a typical CS manager role: you are part people leader, part AI champion, part delivery operator.

This role is central to the buildout of Gorgias AI Services as a dedicated value delivery layer. You'll help design what the future of CS looks like at Gorgias: a model where AI handles execution at scale and humans bring judgment, strategy, and commercial depth. You think like an operator, you're energized by building process and playbooks, and you're technical enough to lead a team that goes deep. Based in Toronto or New York City, reporting to the Head of Customer Experience.

What You'll Do
People Leadership & Coaching

• Lead, coach, and develop a team of up to 10 Enterprise CSMs through regular 1:1s, team rituals, structured performance frameworks, and clear expectations
• Set team OKRs in alignment with CX department strategy, translating high-level goals into actionable, measurable plans
• Own performance management and career development for each direct report - helping your team grow technically, commercially, and professionally
• Upskill your team on emerging technical capabilities, including vibe coding, custom solution building, and AI agent management so that CSMs can go deeper and deliver more value for merchants
• Create a culture of genuine accountability and high standards - you're comfortable making difficult performance decisions and maintaining a high bar across the team, including when that means making hard calls on underperformers

Enterprise Customer Outcomes

• Ensure your team is driving aggressive AI adoption and utilization metrics weekly - helping merchants configure, optimize, and get the most from Gorgias AI Agent
• Own account health (NRR) across a portfolio of enterprise accounts ($30K-$200K+ ARR), ensuring your team is consistently driving measurable customer value
• Guide your team in running high-impact executive business reviews (QBRs) that demonstrate ROI, AI utilization, and strategic alignment with each merchant's goals
• Build a team that surfaces and resolves customer challenges before they require escalation - your goal is a high-functioning team that rarely needs to bring issues up, not one that relies on you as the regular safety net
• Coach CSMs to engage senior merchant stakeholders with commercial depth and outcomes-focused conversations - every interaction should move the needle on value realization, not just maintain presence

AI Strategy & Future of CS Design

• Champion the integration and optimization of Gorgias AI Agent within each merchant's workflows - working with your team to identify automation opportunities, configure AI effectively, and measure deflection and efficiency outcomes
• Help design the future of Customer Success at Gorgias: a model where AI agents handle execution at scale and humans focus on judgment, strategy, and relationship - and actively build the playbooks to make it real
• Embed AI tooling deeply into your team's day-to-day workflows, making AI literacy and AI usage a core expectation and capability within the team
• Drive enablement for your team on new AI product launches, ensuring CSMs can immediately articulate value and implement new features with merchants
• Partner with Product to surface merchant feedback and real-world patterns that shape the roadmap

Operations & Forecasting

• Own team-level forecasting - renewals, expansion pipeline, and churn risk - and deliver accurate, data-backed projections to CS leadership
• Drive operational efficiency across the team: define and iterate on processes, playbooks, and tooling that let your CSMs spend their time where it matters most
• Ensure comprehensive enablement on new product launches so the team can move immediately from announcement to customer impact
• Partner cross-functionally with Sales, Implementation, and Product to ensure seamless handoffs and a cohesive enterprise customer experience
• Build and maintain the reporting infrastructure your team needs to manage account health, identify risk, and track progress against customer goals

Weekly Delivery & Results Cadence

• Run a weekly delivery cadence across your team's book of business - treating customer implementations like a sales pipeline, with weekly reviews, clear milestones, and rigorous next-step accountability at every stage
• Set and track weekly targets for your team: automation adoption progress, active implementations moving forward, and value realization milestones - every week, not every quarter
• Coach CSMs to lead structured, progress-driving customer touchpoints - every interaction should move the needle on an implementation, integration, or adoption goal, not just maintain the relationship
• Bring a sales-minded discipline to delivery: hold weekly pipeline reviews with your team, create visibility into what's stalled, and drive urgency around moving implementations across the finish line
• Manage your team's implementation pipeline with the same rigor a sales leader applies to deals - tracking velocity, identifying blockers, and pushing toward closure with consistency
• Report weekly on delivery momentum: what shipped, what's in flight, what's at risk, and what the team is doing about it

Who You Are

• 7+ years in SaaS CS, implementation, or technical account management; 3+ years managing teams in high-growth environments
• Proven track record owning routcome senterprise accounts ($30K-$200K+ ARR)
• True enterprise operator: you've led CS in genuine enterprise environments - multi-stakeholder accounts, executive relationships, long procurement cycles - and can coach your team to show up at that level
• AI-forward: you've used AI tools consistently in your own work and have a clear point of view on what the next-generation CSM looks like
• Delivery-driven: you own outcomes, not relationships - you run playbooks, track automation targets, and project-manage each customer's journey with discipline
• Commercially sharp: retention and expansion are your problem - you know your book's health, flag risk early, and tie every conversation back to ROI
• Operator mindset: you think in systems, love building repeatable process, and turn ambiguity into clarity
• Exceptional coach: you identify and unlock performance in others - your team members grow meaningfully under your leadership
• Technical: comfortable with APIs, integrations, and automation; able to guide your team toward custom solutions and get hands-on with low-code tooling
• Performance-oriented: you know where you stand, own your metrics, and hold your team to the same standard - GRR, net contraction, and AI interaction volume are your scoreboard, and you build teams that think the same way
• High bar leader: comfortable making difficult performance decisions; you raise the floor of your team over time, not just the ceiling
• Based in Toronto or New York City (hybrid)

Nice to have: Experience in ecommerce or with DTC brands; background in Solution Engineering or Technical Implementation; hands-on experience with AI agent configuration or prompt engineering; consulting or RevOps background.

AI at Gorgias
At Gorgias, AI is a natural extension of how we work and build. Our teams use it every day to research, write, analyze, code, and craft better customer experiences. Everyone has access to premium AI tools (ChatGPT, Claude, Granola & others) and an annual L&D budget to explore new ones.

The real magic happens when we share what we learn. Our #powerup Slack channel is a digital petri dish of new tools and workflows, and each team has AI champions who showcase fresh ideas during weekly company-wide standups, now practically AI demo sessions.

We see AI not as a replacement for creativity or empathy, but as a multiplier, helping us move faster, think deeper, and serve customers better.