Director, Customer Success, Enterprise Account ManagementAbout this positionAbout 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. Good news, we saved you a seat! Qualified applicants will be considered regardless of citizenship, ethnicity, race, colour, religion, gender, gender identity or expression, sexual orientation, disability, age, or veteran status.

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. 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. If you receive a suspicious communication claiming to be from Dialogue, do not respond — report it to [email protected] role asDirector, 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. This leader brings a coaching and empowering management style that develops talent, fosters autonomy, and holds the team accountable to high standards. 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 postureBuilding and nurturing strategic relationships with key stakeholders, including C-suite and executive leadersSupporting 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 executionRepresenting 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 strategyInfluencing 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 needsActing 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 teamsProven experience negotiating and managing relationships with C-suite and senior executives, adopting a trusted advisor mindsetExcellent written and spoken communication skills in both French and EnglishDemonstrated ability to think strategically and critically, assessing opportunities and risks to develop relevant strategiesA track record of performance and success, showing a history of exceeding objectivesA strong bias for action and comfort with ambiguityMastery of a consultative account management approach: understanding the client’s business challenges before proposing a solution, and co-building value over timePrior experience collaborating with a partner or broker network supporting shared clients, and understanding of tripartite relationshipsComfort with digital tools and a strong interest in technology and automationDirect experience with human resources, employee benefits, the insurance industry, or corporate wellness programs is considered a solid asset Access to the Dialogue app and virtual mental health support for you and your familyFully funded insurance, a health spending account, dental coverage, and fitness reimbursement4 weeks vacation, 9 wellness days, and 1 volunteer dayHybrid work: 3 days/week in our Montreal or Toronto offices, excluding remote rolesWork abroad up to 4 weeks/yearIncentive plans, referral bonuses & RRSP matchingLearning via Coursera, external training budget & mentorshipOptional parental leave top-up #

📌 Director, Customer Success, Enterprise Account Management (Winnipeg)
🏢 Dialogue
📍 Winnipeg