Your role asEnterprise 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 advantages:

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

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📌 Enterprise Account Executive, West (British Columbia)
🏢 Dialogue
📍 British Columbia