Senior Manager, Client Success – Enterprise

RiseMe; Montreal (administrative region); Hybrid; CAD 110,000 - 150,000; Full time

Benefits offered by this job

Hybrid work: 3 days/week in Montreal/T

Fully funded insurance

Health spending account

Dental coverage

4 weeks vacation

9 wellness days

1 volunteer day

RRSP matching

Incentive plans

Referral bonuses

Coursera learning & mentorship

Parental leave top-up

Job summary

Dialogue is seeking a Senior Manager, Client Success – Enterprise to act as a client advocate for a strategic segment. You will lead a high-performing team, nurture executive relationships, and shape value-based strategies that drive retention and long-term growth.

This role collaborates with sales, partnerships, and marketing while aligning product and operations to client needs. The role supports hybrid work with offices in Montreal or Toronto, excellent benefits, and ongoing learning

Qualifications

• 5+ years managing complex solutions with cross‑functional teams.
• 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 with a bias for action.
• Consultative account management and client advocacy experience.
• Experience with partner or broker networks and tripartite relationships.
• Comfort with digital tools and interest in technology and automation.
• Direct experience in HR, employee benefits, insurance, or corporate wellness is a strong asset.

Responsibilities

• Lead and grow a team of senior account managers and elevate their advisory posture.
• Build and nurture relationships with C-suite and executives.
• Design value-based account strategies to drive retention and expansion.
• Represent Dialogue at industry events and bring insights back to the team.
• Influence product and operations in line with client needs.
• Align cross-functional teams to client requirements and remove roadblocks.

Skills

Cross-functional leadership

Strategic thinking

C-suite relationship management

Bilingual communication

Job description

Your role asSenior 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