Director of Customer Success (AI)

TL;DR

Director of Customer Success (AI): Leading the Customer Success Management function to drive retention, expansion, and customer advocacy at scale with an accent on building a proactive, lifecycle-driven organization. Focus on integrating AI-augmented workflows into the CS motion, developing high-performing teams, and translating customer insights into actionable product and GTM strategies.

Location: Must be based in the United States or Canada

Salary: $190,000–$210,000

Company

Owner is an AI-native platform providing an all-in-one system for local business owners to manage websites, online ordering, CRM, and POS.

What you will do

• Define and execute the strategy for a proactive, lifecycle-driven Customer Success organization.
• Drive measurable improvements in customer retention, adoption, and expansion across the portfolio.
• Recruit, coach, and develop a high-performing team of CSMs and managers.
• Build and champion AI-augmented workflows for health scoring, predictive analytics, and customer communication.
• Partner with Product, Engineering, and Marketing to translate customer feedback into roadmap improvements.
• Establish clear operating cadences, health scoring frameworks, and scalable playbooks.

Requirements

• Must be based in the United States or Canada
• 8–12+ years of experience in Customer Success or Account Management within SaaS or technology.
• 3–5+ years of leadership experience managing high-performing CSM teams.
• Proven track record of improving retention and driving expansion in recurring revenue businesses.
• Strong data-driven mindset with expertise in KPI frameworks and CS metrics.
• Demonstrated AI fluency with a clear vision for integrating AI into customer success workflows.

Culture & Benefits

• Remote-first workplace environment.
• Comprehensive health coverage.
• Generous pre-IPO equity package.
• Unlimited PTO policy.
• Opportunity to work in a high-growth, AI-native environment.