Senior Manager of Enterprise Customer Success (AI)

TL;DR

Senior Manager of Enterprise Customer Success (AI): Leading a team of Enterprise CSMs to drive AI adoption and value realization for high-ARR merchants with an accent on operational discipline and AI outcomes. Focus on redesigning the Customer Success model to blend AI agents with human strategic judgment and managing complex enterprise relationships.

Location: Hybrid (Must be based in Toronto or New York City)

Salary: CA$155K–CA$207K (Toronto) / $158K–$212K (New York) + Commission

Company

hirify.global is building an AI-powered Conversational Commerce platform that helps ecommerce brands sell, support, and re-engage customers through a unified AI agent.

What you will do

• Lead, coach, and develop a team of up to 10 Enterprise CSMs through performance frameworks and structured career growth.
• Drive aggressive AI adoption and utilization metrics, ensuring merchants optimize the hirify.global AI Agent.
• Own account health and Net Revenue Retention (NRR) for strategic enterprise accounts with ARR from $30K to $200K+.
• Design the future of CS at hirify.global by building playbooks for a value delivery layer where AI handles execution and humans provide strategy.
• Partner cross-functionally with Product, Sales, and Implementation to optimize the enterprise customer journey and roadmap.
• Manage the implementation pipeline with sales-like rigor, tracking velocity and value realization milestones weekly.

Requirements

• 7+ years in SaaS CS, implementation, or technical account management, with 3+ years of people management in high-growth environments.
• Proven experience as an enterprise operator managing multi-stakeholder accounts and senior executive relationships.
• Technical proficiency with APIs, integrations, and low-code automation tooling.
• Strong commercial acumen focusing on retention, expansion, and ROI.
• Experience using AI tools consistently in professional workflows.
• Must be based in Toronto or New York City (hybrid).

Nice to have

• Experience in ecommerce or working with DTC brands.
• Background in Solution Engineering or Technical Implementation.
• Hands-on experience with AI agent configuration or prompt engineering.
• Experience in consulting or RevOps.

Culture & Benefits

• AI-first environment with access to premium tools (ChatGPT, Claude, Granola).
• Annual L&D budget to explore new technologies and professional growth.
• Collaborative knowledge-sharing culture via internal AI champion programs and dedicated Slack channels.
• Commitment to diversity, inclusion, and pay equity across the organization.