Director, Customer Success - NAMER, APAC

Jobtailor; Toronto; On-site; CAD 140,000 - 185,000; Full time

Job summary

Jobtailor is seeking a seasoned Customer Success leader to lead and scale the regional CS organization in Toronto. You will build a cross-functional strategy with Sales, Product, Support, and Marketing to drive adoption and renewals.

You will engage executive sponsors on strategic accounts, mentor CS Managers, and collaborate with global CS leadership to share best practices while maximizing customer outcomes and retention.

Qualifications

• 10+ years in Customer Success or Account Management within enterprise software
• Leadership experience in building scalable customer programs
• Strong collaboration across Sales, Product, Support, and Marketing

Responsibilities

• Lead and scale the regional Customer Success organization.
• Build and execute the customer success strategy aligned with Sales, Product, Support, and Marketing.
• Ensure customers achieve measurable business outcomes through adoption and success planning.
• Personally engage with executive sponsors on strategic accounts and renewal opportunities.
• Lead, coach, and develop a team of Customer Success Managers focused on delivering exceptional outcomes.
• Collaborate with EMEA CS leadership to define and implement best practices worldwide.
• Drive renewals with Sales and identify upsell opportunities through strong customer relationships.

Skills

Customer Success Leadership

Strategic Account Management

Data-Driven Decision Making

Organizational Change Management

Commercial Acumen

Executive Communication

Job description

• Lead and scale the regional Customer Success organization.
• Build and execute the customer success strategy aligned with Sales, Product, Support, and Marketing.
• Ensure customers achieve measurable business outcomes through adoption and success planning.
• Personally engage with executive sponsors on strategic accounts and renewal opportunities.
• Lead, coach, and develop a team of Customer Success Managers focused on delivering exceptional outcomes.
• Collaborate with EMEA Customer Success leadership to define and implement best practices worldwide.
• Drive renewals in collaboration with Sales and identify upsell opportunities through strong customer relationships.

Requirements

• 10+ years of experience in Customer Success or Account Management within enterprise software, with at least 5 years in a leadership role.
• Strong commercial acumen with deep experience supporting strategic renewals and long-term customer retention.
• Strong analytical mindset with the ability to use data to drive decisions.
• Experience leading organizational change and building scalable customer programs.
• Exceptional communication, interpersonal, and organizational skills.
• Experience working across multiple global regions and collaborating with distributed teams.
• Willingness to travel approximately 10–15%.

Core Competencies

Demonstrates expertise in leading Customer Success organizations, developing customer success strategies, and driving measurable business outcomes through effective team management and collaboration across global regions.

Highest-signal resume keywords

• Customer Success Leadership
• Strategic Account Management
• Data-Driven Decision Making
• Organizational Change Management
• Commercial Acumen

ATS Optimization Keywords

Hard Skills

Hard Skills

• Customer Success Strategy
• Enterprise Software Experience
• Renewal Management
• Upsell Opportunity Identification
• Customer Adoption Planning

Soft Skills

• Exceptional Communication
• Interpersonal Skills
• Organizational Skills
• Coaching and Development

Industry Keywords

• Customer Success
• Account Management
• Global Collaboration
• Strategic Renewals
• Customer Retention