Vice President, Client Success

Jobtailor; Mississauga; On-site; CAD 180,000 - 280,000; Full time

Job summary

Jobtailor in Mississauga seeks an accomplished enterprise client success leader to drive company-wide strategies that boost client satisfaction, retention, and growth. The role focuses on executive relationships with unions, trustees, employers, advisors, and plan sponsors, while expanding client relationships to support new products and services.

You will lead a high-performing client success organization, align with Technology and Product teams, and leverage data to improve reporting,

Qualifications

• 15+ years of leadership experience in Benefits Administration, Group Insurance, TPA, Health Benefits, Client Success, or Enterprise Account Management.
• Proven success managing complex client portfolios and strategic relationships.
• Strong understanding of client retention, service delivery, and growth strategies.

Responsibilities

• Develop and execute enterprise-wide client success strategies that drive client satisfaction, retention, and growth.
• Build and maintain executive-level relationships with key clients, unions, trustees, employers, advisors, and plan sponsors.
• Identify opportunities to expand client relationships and support adoption of new products and services.
• Serve as the senior escalation point for complex client matters.
• Champion continuous improvement of the client experience across the organization.
• Partner with Technology and Product teams to enhance and integrate client-facing tools, reporting, analytics, and communications.
• Leverage data and insights to strengthen client engagement and service delivery.
• Establish consistent service standards and performance expectations across client-facing teams.
• Build, coach, and develop a high-performing client success organization.
• Establish KPIs and accountability measures that drive performance and client outcomes.
• Foster a culture of collaboration, client advocacy, operational excellence, and continuous improvement.

Skills

Leadership experience

Client Success Management

Relationship Building

Data-Informed Decision Making

English & French

Tools

Client-Facing Tools

Reporting Tools

Analytics Platforms

Job description

• Develop and execute enterprise-wide client success strategies that drive client satisfaction, retention, and growth
• Build and maintain executive-level relationships with key clients, unions, trustees, employers, advisors, and plan sponsors
• Identify opportunities to expand client relationships and support adoption of new products and services
• Serve as the senior escalation point for complex client matters
• Champion continuous improvement of the client experience across the organization
• Partner with Technology and Product teams to enhance and integrate client-facing tools, reporting, analytics, and communications
• Leverage data and insights to strengthen client engagement and service delivery
• Establish consistent service standards and performance expectations across client-facing teams
• Build, coach, and develop a high-performing client success organization
• Establish KPIs and accountability measures that drive performance and client outcomes
• Foster a culture of collaboration, client advocacy, operational excellence, and continuous improvement

Requirements

• 15+ years of progressive leadership experience in Benefits Administration, Group Insurance, TPA, Health Benefits, Client Success, or Enterprise Account Management
• Proven success managing complex client portfolios and strategic relationships
• Strong understanding of client retention, service delivery, and growth strategies
• Experience leveraging technology and data to enhance client experience and business outcomes
• Strategic, commercially minded, and growth-oriented
• Strong relationship builder with the ability to influence and collaborate effectively across clients, partners, and internal teams
• Collaborative leader who drives alignment across teams and functions
• Data-informed decision maker with strong business and operational acumen
• Results-oriented, accountable, and focused on execution
• Able to navigate complexity while maintaining a client-centric mindset
• Fluency in both English & French (highly desired)
• Experience working with unions, multi-employer benefit plans, trustees, or collectively bargained environments
• Experience in high-growth, private equity-backed, or multi-entity organizations
• Demonstrated success strengthening client relationships while driving retention, expansion, and long-term value creation

Core Competencies

Demonstrates extensive leadership in Client Success and Benefits Administration, with a strong focus on client retention, service delivery, and growth strategies. Proven ability to leverage technology and data to enhance client experiences and drive performance outcomes.

Highest-signal resume keywords

• 15+ Years Leadership Experience
• Client Retention Strategies
• Data-Informed Decision Making
• Relationship Building
• Fluency in English & French

Hard Skills

• Benefits Administration
• Group Insurance
• Client Success Management
• Enterprise Account Management
• KPI Establishment
• Performance Accountability
• Client Portfolio Management
• Strategic Relationship Management
• Operational Excellence
• Data Analysis

Soft Skills

• Collaborative Leadership
• Influencing Skills
• Client Advocacy
• Results Orientation
• Coaching and Development

Industry Keywords

• Health Benefits
• TPA
• Multi-Employer Benefit Plans
• Collectively Bargained Environments
• Private Equity-Backed Organizations

Tools & Technologies

• Client-Facing Tools
• Reporting Tools
• Analytics Platforms