Director, Customer Success
$225,994–$266,011 year
On-siteNew York City, New York, United States
Job Summary
Own the full post-sale journey for Commercial and Enterprise merchants, with direct accountability for Net Revenue Retention across the book. Lead the CS organization end-to-end, including two CS Managers and named-account CSMs, while architecting an AI-first operating model where agents handle execution and humans own outcomes. Set org-wide OKRs, manage the CS budget, and build performance frameworks that drive account health, AI adoption, and expansion. Partner directly with Product and Engineering to shape the AI agent roadmap, ensuring the team pushes boundaries to automate delivery at scale. Report to the COO with visibility into board-level strategy, representing the customer voice in shaping company-wide product and commercial direction.
Required Qualifications
- 10+ years in SaaS Customer Success
- 5+ years leading multi-layered CS orgs
- Proven AI-driven CS leadership
- AI-native mindset
- Full-book commercial ownership
- Org builder
- Leadership presence
- Leader of leaders
- Technical enough
- Systems thinker
- High-bar leader
- Based in Toronto, New York City, San Francisco
Desired Qualifications
- Nice to have: prior experience at an AI-native company
- Nice to have: building an AI-driven service delivery model
- Nice to have: background spanning multiple merchant segments within one organization
- Nice to have: experience partnering directly with Product on an AI roadmap
- Nice to have: ecommerce or DTC industry experience
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