Enterprise Account Executive, West

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
• Excellence

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 [email protected].

AI Disclosure Statement

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.

⚠️ Recruitment Fraud Notice

Dialogue only contacts candidates through official @dialogue.co 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 dialogue.co/en/careers. If you receive a suspicious communication claiming to be from Dialogue, do not respond — report it to [email protected] and verify the role on our official careers page.

Your role as Enterprise Account Executive, West

Reporting to the Vice President of Sales , as Enterprise Account Executive, West you’ll 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. Your job is to spark meaningful conversations, uncover client needs, and bring our Integrated Health Platform to life for organizations. You’re not just selling a solution—you’re telling a story that changes how people access healthcare.

What you'll be doing

• 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 closing
• 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

We'd love to hear from you if you have

• 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
•  Experience working with or alongside brokers is a strong asset

It’s even better if you also have:

• 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
  

At Dialogue, your well-being is our priority

Taking care of others also means taking care of our team! Depending on your role and employment status, you could have access to the following 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