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
The Vice President of Customer Success is the executive leader responsible for building and scaling Lone Wolf Technologies customer value, retention, and growth engine. This role is responsible for transforming the Customer Success organization into a segmented, operationally rigorous, and AI-enabled function that drives customer adoption, supports renewals, improves retention, and delivers a consistent and scalable customer experience across the portfolio.
This leader will redesign the Customer Success operating model to include dedicated Customer Success Managers (CSMs), pooled CSM engagement models, and AI-powered digital coverage for long-tail customers. The Vice President of Customer Success will also lead the implementation and operationalization of a Customer Success platform, establish lifecycle management plays, and strengthen cross-functional alignment across the post-sale customer journey.
The ideal candidate is both a strategic executive and a hands-on operational leader with demonstrated success building scalable Customer Success organizations within complex SaaS environments.

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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