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 Perks 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

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📌 Vice President, Client Success (Ontario)
🏢 Jobtailor
📍 Ontario