Senior Enterprise Client Success Leader

Fleet Glass Services, Inc.; Toronto; Hybrid; CAD 120,000 - 165,000; Full time

Benefits offered by this job

Hybrid work in Toronto/Montreal

Work abroad up to 4 weeks/yr

Insurance + HSA + dental

Vacation: 4 weeks + wellness days + 1

Incentives & RRSP matching

Coursera learning budget

Job summary

Dialogue is seeking a Senior Manager, Client Success – Enterprise to lead a high-impact team serving strategic enterprise clients. Reporting to the VP, you will advocate for clients, develop retention and expansion strategies, and align cross-functional teams to meet complex needs.

This leadership role requires a proven track record with C-suite engagements, thoughtful coaching, and a hands-on, consultative approach.

Qualifications

• 5+ years of experience managing complex solutions with cross-functional teams.
• Proven experience negotiating and managing relationships with C-suite and senior executives.
• Excellent written and spoken communication in French and English.
• Strategic and critical thinking to assess opportunities and risks.
• Track record of exceeding objectives.
• Bias for action and comfort with ambiguity.
• Consultative account management approach with client challenges.
• Experience collaborating with partner or broker networks.
• Affinity for digital tools and technology.
• Experience in HR, employee benefits, insurance, or wellness is a strong asset.

Responsibilities

• Leading and growing a team of senior account managers, elevating their strategic advisor posture.
• Building and nurturing strategic relationships with C-suite and executive leaders.
• Designing value-based account strategies that drive retention, long-term expansion, and client advocacy, while identifying gaps and elevating the overall quality of execution.
• Representing Dialogue at industry events, conferences, and corporate functions to build lasting influence and credibility with HR market leaders, and bringing those insights back internally to inform our strategy.
• Influencing the strategic direction of our tech, clinical, and operational teams based on market signals, in order to evolve Dialogue's offering and stay anchored to real client needs.
• Acting as a central leader in aligning cross-functional teams to our clients’ complex needs, simplifying communication, and removing roadblocks.

Skills

Cross-functional leadership

C-suite relations

Strategic thinking

Bilingual communication

Consultative account management

Partner network

Digital tools

HR/Benefits domain

Team coaching

Client advocacy

Job description

Dialogue is seeking a Senior Manager, Client Success – Enterprise to lead a high-impact team serving strategic enterprise clients. Reporting to the VP, you will advocate for clients, develop retention and expansion strategies, and align cross-functional teams to meet complex needs.

This leadership role requires a proven track record with C-suite engagements, thoughtful coaching, and a hands-on, consultative approach.