Director, Customer Success

We believe conversations will become the #1 way to shop.

At Gorgias, we’re building the platform that makes this real: a unified AI agent that sells, supports, and re-engages customers across the entire journey. Conversational Commerce is the future of ecommerce, and we’re leading that shift.

Our mission is to turn every interaction between a brand and its customers into a relationship: personal, seamless, and intelligent. By combining deep product expertise with the latest in AI, we’re making shopping feel more natural, human, and connected than ever before.

To win, we focus relentlessly on:

• Quality: conversations that feel authentic and on-brand.

• Experience: effortless shopping from chat to checkout.

• Re-engagement: personal, 1-1 dialogue instead of noisy marketing.

The opportunity is massive. As AI reshapes how people buy, Gorgias is building the foundation for the next decade of ecommerce, where every brand has its own intelligent agent and every customer feels understood.

Join us to make Conversational Commerce real.

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.

AI use in Recruiting at Gorgias
By submitting your application, you agree that Gorgias may collect and process your personal data for recruiting, workforce planning, and related purposes. For more information about how we process your data and your rights, please refer to our Applicant Privacy Policy.

Diversity & Inclusion at Gorgias
We’re committed to creating an inclusive environment where everyone can thrive. We welcome applicants from all backgrounds, experiences, and perspectives because diverse teams drive innovation and better decision-making.

If you need accommodations during the application or interview process, please contact us at accommodation@gorgias.com.