Account Executive
Reporting to the Director of Sales, you will be the driving force behind expanding our footprint across central territories. You will generate new business in organizations with up to 1,500 employees, champion the full sales cycle and build relationships with senior leaders.

What You’ll Be Doing

Own the full sales cycle in a net‑new territory, managing the end‑to‑end process from prospecting and qualification to deal strategy, negotiation and close.

Build a pipeline from scratch, developing and executing your own outbound strategy and attaining quota.

Lead multi‑stakeholder sales cycles in complex environments, collaborating with Medical Operations, HR, Finance, Legal and Go‑to‑Market teams.

Maximize territory and market coverage by prioritising accounts, identifying white space and consistently generating net‑new pipeline and revenue through disciplined outbound execution.

Leverage and grow partnerships, sourcing new opportunities and expanding existing partner relationships within your territory while maintaining ownership of the deal cycle.

Represent Dialogue with confidence, presenting our value to senior leaders and executives, both virtually and in person, and steering high‑stakes conversations that influence buying decisions.

We’d Love to Hear from You If You Have

Experience building pipelines from zero and thriving on prospecting, cold calling and breaking into new accounts.

A track record of moving fast and adapting quickly in ambiguous, fast‑moving environments.

Executive presence and professionalism, with the ability to sell a high‑impact solution to senior HR, Finance and executive stakeholders.





A passion for selling a solution that removes barriers to physical and mental healthcare and delivers real value to employees and organizations across Canada.

5+ years of B2B sales experience, ideally in benefits, insurance or a similarly complex environment, with a history of leading consultative sales cycles and influencing outcomes across HR, Finance and leadership teams.

Experience working with or alongside brokers.

It’s Even Better If You Also Have

Experience working with third‑party administrators (TPAs), insurance brokers or 3rd‑party channel sales.

Experience selling to HR, Operations and/or Finance leaders.

A background in the insurance or employee benefits industry.

Experience using Salesforce or a similar CRM system.

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 per week in our Montreal or Toronto offices (remote not applicable).

Work abroad up to 4 weeks per year.

Incentive plans, referral bonuses and RRSP matching.

Learning via Coursera, an external training budget and mentorship.

Optional parental leave top‑up.

We’re a proud equal‑opportunity employer. Qualified applicants will be considered without regard to citizenship, ethnicity, race, religion, gender, gender identity or expression, sexual orientation, disability, age, or veteran status. If you require qualified accommodations, please contact [email protected].

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📌 Account Executive, Central (Ontario)
🏢 Dialogue
📍 Ontario