Director of Customer Success (AI)

TL;DR

Director of Customer Success (AI): Architecting and leading an AI-first customer success organization for a high-growth SaaS platform with an accent on NRR, commercial strategy, and AI-driven automation. Focus on building a scalable operating model where AI agents handle high-volume execution while human teams drive strategic relationships and commercial outcomes.

Location: Must be based in or able to work from Toronto, New York City, or San Francisco (Hybrid)

Compensation: $235,410 – $277,095 base + variable

Company

hirify.global is an AI-native platform transforming conversational commerce by enabling brands to provide seamless, intelligent customer support and sales experiences.

What you will do

• Own the end-to-end CS organization chart, including hiring, structure, and span of control for Commercial and Enterprise segments.
• Redesign the CS function into an AI-first model where AI agents handle execution and humans focus on commercial depth and judgment.
• Directly coach and develop CS Managers to ensure high performance and organizational growth.
• Manage the full CS budget, making strategic tradeoffs between human capacity and AI investment.
• Drive NRR across the merchant base by implementing segment-specific strategies and high-impact executive business reviews.
• Partner with Product and Engineering leadership to shape the AI agent roadmap based on frontline merchant signals.

Requirements

• 10+ years in SaaS Customer Success with 5+ years leading multi-layered organizations.
• Proven experience in AI-driven CS leadership, having scaled models where technology drives outcomes.
• Full-book commercial ownership with a track record of managing NRR/GRR across large, segmented bases.
• Org-building expertise, specifically in redesigning or building functions from the ground up.
• Technical fluency in AI agent capabilities, limitations, and roadmap strategy.
• Must be based in Toronto, New York City, or San Francisco and able to work in a hybrid capacity.

Nice to have

• Prior experience at an AI-native company or building AI-driven service delivery models.
• Background spanning multiple merchant segments within one organization.
• Experience partnering directly with Product on AI roadmaps.
• Ecommerce or DTC industry experience.

Culture & Benefits

• Access to premium AI tools (ChatGPT, Claude, Granola) for daily workflows.
• Annual L&D budget for exploring new technologies and professional growth.
• Collaborative environment with dedicated AI champions and company-wide AI demo sessions.
• Commitment to an inclusive, diverse team culture that drives innovation.