Vice President, Customer Success

Lone Wolf Technologies

Lone Wolf Technologies

Sales & Business Development, Customer Service

Cambridge, ON, Canada

CAD 220k-260k / year

Posted on May 20, 2026

ESSENTIAL RESPONSIBILITIES & DUTIES:

    Customer Success Strategy & Operating Model

    • Design and implement a segmented Customer Success model supporting strategic, scaled, and long-tail customer segments.
    • Establish engagement models including named CSM coverage, pooled customer management, and digital or AI-driven customer motions.
    • Lead customer segmentation, capacity planning, and book-of-business design aligned to customer value, complexity, and growth opportunity.
    • Define service levels, ownership boundaries, and operational standards across all customer segments.
    • Drive organizational transformation and change management initiatives to support evolving customer engagement models.

      • AI & Customer Success Platform Leadership

      • Evaluate, select, implement, and operationalize a Customer Success platform integrated with CRM, Support, billing, and product usage systems.
      • Develop health score frameworks, customer lifecycle workflows, segmentation logic, and reporting standards.
      • Define and execute an AI strategy for Customer Success, including workflow automation, risk identification, digital engagement, and productivity optimization.
      • Build scalable AI-enabled customer engagement models that improve coverage, prioritization, and proactive outreach.

        • Customer Lifecycle & Retention Management

        • Develop standardized lifecycle plays for onboarding, adoption, renewal readiness, risk mitigation, customer save motions, and expansion opportunities.
        • Ensure lifecycle plays are embedded into workflows and systems for consistent execution and measurement.
        • Build proactive risk identification and escalation processes to improve customer retention and renewal predictability.
        • Partner with Sales and Account Management teams to identify expansion opportunities and customer growth signals.
        • Drive improvements in Gross Revenue Retention (GRR), Net Revenue Retention (NRR), adoption, and customer health metrics.

          • Customer Capability & Issue Resolution

          • Expand Customer Success capabilities to directly resolve a broader range of customer issues and reduce unnecessary escalations to Support.
          • Partner with Support, Product, Services, Training, and Documentation teams to improve customer outcomes and reduce friction in the customer journey.
          • Develop technical and specialist capabilities within the Customer Success organization where appropriate.
          • Improve customer continuity and speed-to-resolution through stronger internal enablement and process alignment.

            • Leadership & Operational Excellence

            • Build and lead a high-performing Customer Success leadership team.
            • Establish KPIs, operating cadences, governance processes, and performance management frameworks.
            • Drive a culture of accountability, continuous improvement, operational rigor, and customer-centric execution.
            • Conduct regular business reviews and executive reporting on customer health, retention, adoption, and operational performance.
            • Collaborate cross-functionally with Product, Revenue Operations, Finance, Services, Support, and Sales leadership teams.

QUALIFICATIONS & EXPERIENCE:

    • Bachelor’s degree in Business, Marketing, Technology, or related field required; advanced degree preferred.
    • 10+ years of progressive leadership experience in Customer Success, Account Management, or post-sale SaaS operations.
    • Executive leadership experience within a SaaS or technology organization with complex customer segmentation and retention models.
    • Proven experience redesigning or scaling Customer Success operating models across high-touch and tech-touch segments.
    • Experience implementing and operationalizing Customer Success platforms and workflow automation tools.
    • Strong understanding of AI, automation, digital engagement strategies, and customer lifecycle orchestration.
    • Demonstrated success improving retention, adoption, and customer outcomes through operational excellence and scalable processes.
    • Strong executive presence with the ability to influence and collaborate across senior leadership teams.
    • Experience leading organizational transformation and change management initiatives

KEY PERFORMANCE INDICATORS (KPIs):

  • Gross Revenue Retention (GRR)
  • Net Revenue Retention (NRR)
  • Customer adoption and product utilization
  • Customer health score improvement
  • Renewal readiness and churn reduction
  • Expansion opportunity contribution
  • Customer satisfaction and engagement metrics
  • AI adoption and workflow efficiency improvements
  • Operational scalability and process consistency

WHAT SUCCESS LOOKS LIKE:

    • A clearly defined and scalable Customer Success operating model is successfully implemented.
    • AI-enabled customer workflows improve coverage, prioritization, and proactive customer engagement.
    • Customer Success platform adoption becomes embedded into daily operational execution.
    • Standardized lifecycle plays drive consistency across onboarding, adoption, renewals, and expansion.
    • Customer Success resolves a broader range of customer issues directly, improving continuity and reducing handoffs.
    • Retention, adoption, and customer growth metrics improve measurably over time.
    • The Customer Success organization operates with strong accountability, measurable performance standards, and operational discipline

220000 - 260000 CAD a year

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