Director, Customer Success, Enterprise Account Management

About Dialogue

Dialogue is the #1 virtual care provider in Canada. By developing our Integrated Health Platform, we provide exceptional online health and wellness programs (primary care, mental health, iCBT, EAP, and wellness) to organizations that want to improve the wellness of their employees and families.

When it comes to our work, we set the bar high. Together, we’re transforming health and helping millions improve their well‑being. We’re firm believers that great people don’t settle on:

• Impact
• Community
• Growth
• Excellence

Feel like you can make a difference? Good news, we saved you a seat!

Equal‑Opportunity Employer

Come as you are. As a proud equal‑opportunity employer, Dialogue is dedicated to creating a diverse and inclusive workplace for everyone. Qualified applicants will be considered regardless of citizenship, ethnicity, race, colour, religion, gender, gender identity or expression, sexual orientation, disability, age, or veteran status. Applicants who require specialized accommodation are encouraged to contact accessibility@dialogue.co.

AI Disclosure Statement

To ensure an efficient and fair review process, we utilize artificial intelligence tools to assist in the initial screening and assessment of applicants for this role.

Recruitment Fraud Notice

Dialogue only contacts candidates through official @dialogue.co email addresses. We never request payment, gift cards, or personal financial information at any stage of hiring, and we never extend an offer without a structured interview process. All open roles are listed exclusively at dialogue.co/en/careers. If you receive a suspicious communication claiming to be from Dialogue, do not respond — report it to jobs@dialogue.co and verify the role on our official careers page.

Your role as Director, Customer Success, Enterprise Account Management

Reporting to Melissa Trottier, Vice President, Customer Success, the Director, Customer Success, Enterprise Account Management 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

Please note that as we serve customers across Canada, bilingualism is essential for this position. You may be required to communicate in French and English.

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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