Account Executive, West

Company Overview

Dialogue is Canada’s leading virtual care provider. By developing our Integrated Health Platform, we provide online health and wellness programs—including primary care, mental health, iCBT, EAP, and wellness—to organizations that want to improve the well-being of their employees and families.

We are firm believers that great people don’t settle on impact, community, or growth
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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.

Reporting to the Vice President of Sales, the Account Executive – West will be the driving force behind expanding our footprint across western territories. You’ll thrive in a fast‑moving, high‑growth environment where hustle, grit, and the ability to pivot are key.

• Own the full sales cycle in a net‑new territory: Manage end‑to‑end sales from prospecting and qualification to deal strategy, negotiation, and close with organizations up to 1,500 employees.
• Build pipeline from scratch: Develop and execute your own outbound strategy, working closely with Business Development and Partnerships, and ultimately owning pipeline creation and quota attainment.
• Sell strategically in complex environments: Lead multi‑stakeholder sales cycles, collaborating internally with Medical Operations, HR, Finance, Legal, and Go‑to‑Market teams.
• Maximize territory and market coverage: Prioritize accounts, identify whitespace, and consistently generate net‑new pipeline and revenue through disciplined outbound execution.
• Leverage and grow partnerships: Collaborate with the Partnerships team to source new opportunities and expand existing partner relationships within your territory.
• Represent Dialogue with confidence: Present Dialogue’s value to senior leaders and executives, both virtually and in person, and lead high‑stakes conversations that influence buying decisions.
• Manage the end‑to‑end sales process: Identify, qualify, capture, and close complex sales within companies that have fewer than 1,500 employees.

• Thriving in net‑new sales: You’re energized by building a pipeline from zero and take pride in creating opportunities in a competitive market.
• Moving fast and adapting quickly: You operate well in ambiguous, fast‑moving environments and recalculate quickly when things change mid‑cycle.
• Sell with credibility and conviction: You bring strong executive presence and professionalism to every interaction, selling high‑impact solutions to senior HR, Finance, and Executive stakeholders.
• Motivated by meaningful outcomes: You’re excited to sell a solution that removes barriers to physical and mental healthcare and delivers real value to employees and organizations across Canada.
• Having experience selling complex B2B solutions: 5+ years of B2B sales experience, ideally in benefits, insurance, or a similarly complex environment, with multi‑stakeholder deals and consultative sales cycles.
• Experience working with or alongside brokers is a strong asset.

• Experience with third‑party administrators, insurance brokers, or channel sales.
• Experience selling to HR, Operations, and/or Finance leaders.
• A background in the insurance or employee benefits industry.
• Experience with Salesforce or a similar CRM.

• 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 for non‑remote roles.
• Work abroad up to 4 weeks/year.
• Incentive plans, referral bonuses, and RRSP matching.
• Learning through Coursera, an external training budget, and mentorship.