Enterprise Account Executive – Central

Dialogue; Toronto; On-site; CAD 100,000 - 125,000; Full time

Job summary

A leading virtual care provider in Toronto is seeking an Enterprise Account Executive to engage with large organizations across Central Canada. The ideal candidate will have over 3 years of B2B sales experience, exceptional communication skills, and a mission-driven mindset. The role includes managing sales cycles, building pipelines, and collaborating with various teams to drive enterprise growth. This position offers competitive benefits including hybrid work, vacation, and wellness support.

Benefits

Access to the Dialogue app for mental health support

Fully funded insurance and health spending account

4 weeks vacation and wellness days

Incentive plans and RRSP matching

Learning opportunities via Coursera

Qualifications

• 3+ years of enterprise B2B sales experience.
• Exceptional communication and storytelling abilities.
• A consultative approach to understanding client needs.

Responsibilities

• Own the end-to-end sales cycle targeting companies with 2,000+ employees.
• Build and manage a pipeline of high-value opportunities.
• Deliver tailored pitches to executive-level stakeholders.
• Collaborate cross-functionally to ensure alignment.
• Document activity in CRM (Salesforce) for pipeline maintenance.
• Partner with Marketing to support enterprise growth.

Skills

Enterprise B2B sales experience

Communication and storytelling

Consultative approach

High professionalism

Tools

Salesforce

Job description

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

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 [e-mail] .

Your role as Enterprise Account Executive – Central

Reporting to the Director, Enterprise Accounts, your mission will be to engage with enterprise‑level organizations (2,000+ employees) across Central Canada. You will focus on building strategic relationships with some of the country’s most prominent employers, championing our virtual healthcare solutions to positively impact the lives of Canadians.

We’re looking for a high‑performing, purpose‑driven sales professional who thrives in a dynamic environment and is excited by the opportunity to sell meaningful solutions in the health and wellness space.

What you’ll be doing:

• Own the end‑to‑end sales cycle: From prospecting and qualification to solution development and closing, targeting companies with 2,000+ employees across Central Canada
• Build and manage a pipeline of high‑value opportunities by leveraging inbound leads, partnerships, and proactive outreach
• Present with impact: Confidently deliver tailored pitches and demos to executive‑level stakeholders (virtually and in‑person), positioning Dialogue as a strategic healthcare partner
• Collaborate cross‑functionally with teams across Sales, Business Development, Marketing, Customer Success, Medical Operations, Finance, HR, and Legal to ensure alignment and deal velocity
• Document activity in CRM (Salesforce) and follow a structured sales methodology to maintain pipeline hygiene, forecast accurately, and share insights across the team
• Partner with Marketing to co‑develop content and campaigns to support enterprise growth

We’d love to hear from you if you have:

• A mission‑driven mindset : You’re passionate about improving access to quality physical and mental healthcare for Canadians
• 3+ years of enterprise B2B sales experience, ideally with a focus on complex, strategic solution‑selling and executive stakeholder management
• Exceptional communication and storytelling abilities , with a knack for translating complex ideas into clear, compelling messages
• A consultative approach : You lead with curiosity and insight, understanding business needs before presenting solutions
• High professionalism and executive presence : You represent Dialogue with passion and integrity, always putting the client experience first

Bonus points if you have:

• Experience in the healthcare, benefits, or insurance industry
• Experience selling to HR, Operations, and/or Finance leaders
• Familiarity with Salesforce and other sales enablement tools

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