- 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 Advantages 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 (Mississauga)
🏢 Jobtailor
📍 Mississauga