Director of Customer Success, Gorgias

• 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)

Desirable

• 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
• 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
• 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
• 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
• 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