Enterprise Account Executive – Central

Dialogue; Toronto; Hybrid; CAD 75,000 - 100,000; Full time

Job summary

Join a leading virtual healthcare provider as an Enterprise Account Executive in Toronto. You will drive enterprise-level sales across Central Canada, building strategic relationships and presenting impactful solutions to improve access to quality healthcare for Canadians. Ideal candidates are mission-driven sales professionals with extensive B2B experience and exceptional communication skills.

Benefits

Access to the Dialogue app and virtual mental health support

Fully funded insurance and health spending account

4 weeks vacation and 9 wellness days

Hybrid work flexibility

Work abroad opportunities

Incentive plans and RRSP matching

Learning and development opportunities

Optional parental leave top-up

Qualifications

• 8+ years of enterprise B2B sales experience.
• Exceptional communication and storytelling abilities.
• Consultative approach to understand business needs.

Responsibilities

• Own the end-to-end sales cycle for enterprise-level organizations.
• Build and manage a pipeline of high-value opportunities.
• Delivery of tailored pitches and demos to executive-level stakeholders.

Skills

Communication

Storytelling

Consultative Selling

Executive Presence

Tools

Salesforce

Job description

Join to apply for the Enterprise Account Executive – Central role at Dialogue

Join to apply for the Enterprise Account Executive – Central role at Dialogue

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
• 8+ 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 withSalesforce and other sales enablement tools.

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


• 8+ 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 withSalesforce 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, 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 Toronto office


• 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

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 [e-mail] .

Seniority level

• Seniority level

  Mid-Senior level

Employment type

• Employment type

  Full-time

Job function

• Job function

  Sales and Business Development

• Industries

  Technology, Information and Internet

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