Account Executive

Dialogue • Toronto, ON

31d • Hybrid

About The Position

Reporting to the Director of Sales, as Account Executive you’ll be the driving force behind expanding our footprint across eastern territories. You’ll thrive in a fast-moving, high-growth environment where hustle, grit, and the ability to pivot are key. Your job is to spark meaningful conversations, uncover client needs, and bring our Integrated Health Platform to life for organizations under 1500 employees. You’re not just selling a solution—you’re telling a story that changes how people access healthcare.

Requirements

• Thrive in net-new sales: You’re energized by building a pipeline from zero. You’re comfortable prospecting, cold calling, and breaking into new accounts, and you take pride in creating your own opportunities in a competitive market.
• Move fast and adapt quickly: You operate well in ambiguous, fast-moving environments and can adjust your approach as you learn. When things change mid-cycle, you don’t stall—you recalibrate and keep moving.
• Sell with credibility and conviction: You bring strong executive presence and professionalism to every interaction. You know how to sell a serious, high-impact solution to senior HR, Finance, and Executive stakeholders—and you understand that how you show up matters.
• Are 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.
• Have experience selling complex B2B solutions: You bring 5+ years of B2B sales experience, ideally in benefits, insurance, or a similarly complex environment. You’ve navigated multi-stakeholder deals, led consultative sales cycles, and influenced outcomes across HR, Finance, and leadership teams.

Nice To Haves

• Experience working with or alongside brokers is a strong asset.
• Experience working with third-party administrators (TPAs), insurance brokers, and/or 3rd party channel sales.
• Experience selling to HR, Operations, and/or Finance leaders.
• A background in the insurance or employee benefits industry.
• Experience working with Salesforce or similar CRMs.

Responsibilities

• Own the full sales cycle in a net-new territory: You’ll manage the end-to-end sales process—from prospecting and qualification to deal strategy, negotiation, and close—selling into organizations with up to 1,500 employees.
• Build pipeline from scratch: You’ll develop and execute your own outbound strategy, working closely with Business Development and Partnerships, but ultimately owning pipeline creation and quota attainment.
• Sell strategically in complex environments: You’ll lead multi-stakeholder sales cycles, collaborating internally with teams across Medical Operations, HR, Finance, Legal, and Go-to-Market to move deals forward and remove friction.
• Maximize territory and market coverage: You’ll prioritize accounts, identify whitespace, and consistently generate net-new pipeline and revenue through disciplined outbound execution.
• Leverage and grow partnerships: You’ll collaborate with the Partnerships team to source new opportunities and expand existing partner relationships within your territory, while maintaining ownership of the deal cycle.
• Represent Dialogue with confidence: You’ll present Dialogue’s value to senior leaders and executives, both virtually and in person, and feel comfortable leading high-stakes conversations that influence buying decisions.
• Manage the end-to-end sales process: This includes, but is not limited to identifying, qualifying, capturing, and closing complex sales within companies that have fewer than 1500 employees.

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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed