Enterprise Account Executive â Central

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

Job description

Your role as Enterprise Account Executive Central

Reporting to the Director of Enterprise Accounts, your mission will be to engage with enterprise-level organizations (2000 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 lives. We are looking for a high-performing, purpose-driven sales professional who thrives in a dynamic environment and is excited about selling 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 2000 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 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, 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, and RRSP matching.
• Learning via Coursera, external training budget, and 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 aiming to improve employee and family wellness.

We set high standards in our work. Together, we're transforming health and helping millions improve their well-being. We believe that great people don't settle for less on:

Impact, Community, Growth, and Excellence.

If you feel 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. Qualified applicants will be considered regardless of citizenship, ethnicity, race, color, religion, gender, gender identity or expression, sexual orientation, disability, age, or veteran status. Applicants requiring specialized accommodation are encouraged to contact us.

Required Experience :

Key Skills

SAAS, Customer Service, Cloud, Healthcare, Account Management, CRM, Salesforce, Infrastructure, Client Relationships, New Customers, Territory, Trade shows, Sales Goals, Sales Process, Analytics

Employment Type : Full Time

Experience : 8 years

Vacancy : 1