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 Perks 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 (Winnipeg)
🏢 Jobtailor
📍 Winnipeg