Director, Customer Success

📋 Description

• Own CS org for Commercial & Enterprise; two CS Managers report to you.
• Build AI-first CS with humans handling strategic work.
• Own NRR; track renewals, expansions, churn risk; report to COO.
• Lead CS budget, hiring, tooling; balance human vs AI.
• Coach managers; set OKRs; build career framework.
• Collaborate with Product/Engineering on AI roadmap.

🎯 Requirements

• 10+ years in SaaS CS; 5+ years leading multi-layer CS orgs
• Proven AI-driven CS leadership; tech-driven outcomes
• AI-native mindset; automation-first delivery
• Full-book ownership of NRR/GRR across large merchant base
• Org-builder; comfortable with ambiguity and greenfield scope
• Based in Toronto, New York City, San Francisco (hybrid)

🎁 Benefits

• Annual L&D budget to explore new AI tools
• Access to premium AI tools (ChatGPT, Claude, Granola)
• AI champions and weekly AI demos across teams
• Hybrid-friendly locations: Toronto, NYC, SF