About the Team

Customer Success at Gorgias covers our Commercial and Enterprise merchants and sits at the center of a fundamental redesign of what CS means in an AI-native company. We're rebuilding the org from the ground up around a simple premise: AI agents handle high-volume execution, and humans own outcomes, judgment, and commercial depth. This isn't an incremental evolution of a support function: it's the construction of a new operating model where AI is the primary delivery engine.

We've already proven pieces of this model in our Enterprise segment. Now we need a leader to take that vision across the function: architecting a CS organization where AI does the heavy lifting and humans focus on the relationships, judgment calls, and commercial outcomes that AI can't own. As Head of CSM, you are responsible for delivering value at scale in the age of AI: pushing the boundaries to automate as much as possible to deliver the best experience for our merchants.

About the Role

As Director, Customer Success, you'll own the full post-sale journey for Gorgias's Commercial and Enterprise merchants, with direct accountability for Net Revenue Retention (NRR) across that book. SMB is mainly product-led growth and only needs light oversight from this role. You'll lead the CS organization end-to-end: 2 CS Managers report directly to you, one leading Commercial and one leading Enterprise, and the CSMs covering our few named accounts also report directly to you.

This is an architect role as much as a leadership role. You're not inheriting a finished org chart: you're building the next generation of Customer Success at Gorgias, where AI agents handle high-volume execution and your managers and CSMs bring strategic depth, commercial judgment, and the human relationships AI can't replace. You'll report directly to the COO, with the scope and budget to (re)build the CS org from the ground up.

What You'll Do
Organizational Leadership

Own the CS org chart across Commercial and Enterprise: 2 CS Managers plus the named-account CSMs, setting structure, span of control, and hiring plans as the org scales with AI-driven leverage
Directly coach and develop your CS Managers, holding them accountable for the performance, growth, and output of their teams
Set org-wide OKRs across Commercial and Enterprise, translating company strategy into segment-specific execution plans
Own the CS budget end-to-end (headcount, tooling, and program spend), making the tradeoffs between human capacity and AI investment
Build the performance management and career framework for CSMs and managers across both segments
Create a culture of genuine accountability and high standards across the org, including making difficult performance decisions when needed

Commercial & Enterprise Outcomes & NRR

Own NRR across Commercial and Enterprise, with segment-specific strategies rather than a one-size-fits-all playbook
Ensure your managers and their CSMs are consistently driving account health, AI adoption, and expansion across both segments
Personally engage with the most strategic accounts and escalations, bringing senior judgment to the relationships that matter most
Build the reporting and forecasting infrastructure to track renewals, expansion pipeline, and churn risk across the full book, with clear visibility for the COO and leadership team
Guide your managers in running high-impact executive business reviews that demonstrate ROI and AI utilization across both segments

Architecting AI-First Customer Success

Own the vision and execution for redesigning Customer Success as an AI-first function, where AI agents handle execution at scale and humans own outcomes
Partner directly with Product and Engineering leadership to shape the AI agent roadmap, bringing frontline signal from Commercial and Enterprise merchants
Deliver value at scale in the age of AI: push the boundaries to automate as much as possible to deliver the best experience for our merchants
Build AI literacy from the ground up across the org: every CSM and manager should be fluent in configuring, evaluating, and improving AI-driven outcomes
Represent Customer Success in cross-functional AI strategy conversations at the leadership level, with direct influence over the AI product roadmap

Leadership Partnership & Company-Wide Impact

Report directly to the COO, with regular visibility into company leadership and board-level conversations about CS performance and strategy
Partner with Sales, Implementation, and Product leadership to build a cohesive post-sale experience across the entire customer lifecycle
Represent the voice of the customer at the leadership level, shaping company strategy and the product roadmap
Own reporting to company leadership on CS health, AI adoption, and organizational progress

Who You Are

10+ years in SaaS Customer Success, with 5+ years leading multi-layered CS orgs: managing managers, not just individual contributors
Proven AI-driven CS leadership: you've built or scaled a CS model where technology, not just headcount, drove outcomes
AI-native mindset: you default to automation first and treat AI as the primary delivery engine, not a bolt-on
Full-book commercial ownership: track record owning NRR/GRR across a large, segmented merchant base; you understand Commercial and Enterprise as genuinely different motions
Org builder: experience building a CS org from the ground up or fundamentally redesigning an existing one; you're comfortable with ambiguity and greenfield scope
Leadership presence: comfortable operating with direct COO and board-level visibility, and owning a budget with real tradeoffs
Leader of leaders: you've coached managers, not just ICs, and know how to scale a leadership bench
Technical enough: you have a real point of view on AI agent capabilities, limitations, and roadmap, and can hold your own in product conversations
Systems thinker: you build repeatable process and infrastructure rather than relying on heroics
High-bar leader: comfortable making difficult organizational and performance decisions as you (re)build the function
Based in Toronto, New York City, San Francisco (each are hybrid)

Nice to have: prior experience at an AI-native company or building an AI-driven service delivery model; background spanning multiple merchant segments within one organization; experience partnering directly with Product on an AI roadmap; ecommerce or DTC industry experience.

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.

Gorgias

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Director, Customer Success