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Added 14 mins ago
Director, Enterprise AI Strategy & Transformation
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Toronto, ON
Full-time
Reporting to the Chief Financial Officer, the Director, Enterprise AI Strategy & Transformation leads the development and execution of the organization’s enterprise AI strategy and…
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Dialogue

Senior Manager, Client Success – Enterprise

Toronto, ON, Canada
Montreal, QC, Canada

Experience: 5+ years of experience managing complex solutions with cross-functional teams
Posting language: English
Posted: Sep 24, 2026

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Original job description

Your role as Senior Manager, Client Success – Enterprise

Reporting to Melissa Trottier, Vice President, Customer Success, the Senior Manager, Client Success – Enterprise has a mission to serve as a client advocate and trusted advisor for a highly strategic segment of Dialogue’s clientele, driving sustainable growth and ensuring long-term success.

This position requires an experienced leader, capable of managing strategic relationships, but above all, inspiring, mobilizing, and developing their team. The Director will play a key role in talent development, creating a collaborative environment, and achieving ambitious collective goals. They will be responsible for designing and implementing effective retention and engagement strategies, while ensuring our solutions optimally meet the complex and evolving needs of our clients. This leader brings a coaching and empowering management style that develops talent, fosters autonomy, and holds the team accountable to high standards.

The Director will be accountable for achieving a defined growth objective, ensuring the team generates sustainable and measurable value for both our clients and Dialogue. In close collaboration with the sales, partnerships, and marketing teams, this individual will act as the spokesperson for our most strategic clients, while strengthening team cohesion and performance to drive sustained growth.

What you'll be doing

Leading and growing a team of senior account managers, elevating their strategic advisor posture
Building and nurturing strategic relationships with key stakeholders, including C-suite and executive leaders
Supporting the team in 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

We'd love to hear from you if you have

5+ years of experience managing complex solutions with cross-functional teams
Proven experience negotiating and managing relationships with C-suite and senior executives, adopting a trusted advisor mindset
Excellent written and spoken communication skills in both French and English
Demonstrated ability to think strategically and critically, assessing opportunities and risks to develop relevant strategies
A track record of performance and success, showing a history of exceeding objectives
A strong bias for action and comfort with ambiguity
Mastery of a consultative account management approach: understanding the client’s business challenges before proposing a solution, and co-building value over time
Prior experience collaborating with a partner or broker network supporting shared clients, and understanding of tripartite relationships
Comfort with digital tools and a strong interest in technology and automation
Direct experience with human resources, employee benefits, the insurance industry, or corporate wellness programs is considered a strong asset

At Dialogue, your well-being is our priority

Taking care of others also means taking care of our team! Depending on your role and employment status, you could have access to the following benefits:

Access to the Dialogue app and virtual mental health support for you and your family
Fully funded insurance, a health spending account, dental coverage, and fitness reimbursement
4 weeks vacation, 9 wellness days, and 1 volunteer day
Hybrid work: 3 days/week in our Montreal or Toronto offices, excluding remote roles
Work abroad up to 4 weeks/year
Incentive plans, referral bonuses & RRSP matching
Learning via Coursera, external training budget & mentorship
Optional parental leave top-up

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More about this job

Responsibilities

The Senior Manager will lead a team of account managers to drive retention, growth, and strategic value for key enterprise clients. They will act as a central leader in aligning cross-functional teams to meet complex client needs while fostering a culture of high performance and talent development.

Requirements

Candidates must have 5+ years of experience managing complex solutions and negotiating with C-suite executives. A strong background in consultative account management and the ability to work effectively across cross-functional teams is required.

Skills

Strategic account management
Team leadership
Client advocacy
Cross-functional collaboration
Negotiation
Strategic planning
Talent development
Coaching
Consultative selling
Market analysis
Employee benefits
Corporate wellness
Communication
Technology adoption

Benefits

Dialogue app access
Virtual mental health support
Fully funded insurance
Health spending account
Dental coverage
Fitness reimbursement
4 weeks vacation
9 wellness days
1 volunteer day
Hybrid work
Work abroad up to 4 weeks/year
Incentive plans
Referral bonuses
RRSP matching
Learning budget
Mentorship
Parental leave top-up

Visa sponsorship

Not detected in the job text

Hiring contact

Melissa Trottier

Keywords

Client Success
Enterprise
Account Management
Strategic Planning
Leadership
C-suite
Retention
Growth
Cross-functional
Human Resources
Employee Benefits
Insurance
Corporate Wellness
Consultative Approach
Automation
Digital Tools
Stakeholder Management
Value-based Strategy
Market Insights
Talent Development

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