Director, Customer Success, Enterprise Account Management

Director, Customer Success, Enterprise Account Management About this position

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

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

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

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. Dialogue only contacts candidates through official  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  If you receive a suspicious communication claiming to be from Dialogue, do not respond – report it to  and verify the role on our official careers page.

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.

• 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.

• 5+ years of experience managing complex solutions with cross‑functional teams.
• Prov…