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 accessibility@dialogue.co.

Your role as Director, Mid-Market Sales

Dialogue is looking for a hands-on Director, Mid-Market Sales to lead, coach, and inspire a team of Account Executives responsible for generating net-new ARR. This is a highly people-focused leadership role, ideal for someone who thrives on developing talent, building high-performing teams, and driving results in a fast-paced, growth-oriented environment.

You’ll play a critical role in scaling our mid-market sales motion—driving consistent pipeline creation, improving deal velocity, and ensuring your team is set up for long-term success. This role partners closely with cross-functional teams to bring complex deals across the finish line and continuously improve how we sell.

What you'll be doing

Lead & Coach a High-Performing Sales Team

• Directly manage, mentor, and develop a team of Mid-Market Account Executives focused on net-new ARR
• Foster a culture of accountability, curiosity, collaboration, and continuous improvement
• Provide hands-on coaching through deal reviews, pipeline inspections, call shadowing, and role plays
• Lead and support AEs in building disciplined outbound motions and consultative, value-based selling skills
• Recruit, onboard, and ramp new AEs while maintaining consistent performance standards across the team

Drive Revenue & Execution Excellence

• Be hands-on in the sales process, actively supporting AEs on strategy, deal execution, and closing
• Own team performance across ARR targets, pipeline coverage, conversion rates, and forecast accuracy
• Ensure strong pipeline generation through outbound, broker-led, and partner-supported motions
• Help AEs navigate complex, multi-stakeholder sales cycles and RFP processes
• Identify trends, risks, and opportunities in the pipeline and proactively course-correct

Cross-Functional Collaboration

• Partner closely with Business Development to ensure strong pipeline quality and seamless handoffs
• Collaborate with Marketing on campaigns, messaging, and territory strategy
• Work with Customer Success to support smooth handoffs and long-term customer value
• Align with Medical Operations, Finance, HR, and Legal to remove friction and accelerate deal velocity
• Act as the voice of the field, sharing feedback to improve processes, tooling, and go-to-market strategy

Build, Scale & Improve

• Help refine our mid-market sales playbook, processes, and enablement
• Champion best practices in forecasting, CRM hygiene, and performance management
• Lead with empathy while maintaining a strong performance bar

We'd love to hear from you if you have

• 2+ years managing mid-market, net-new ARR sales teams
• Proven success in SaaS, health tech, benefits, or insurance
• Strong coaching skills to develop and inspire quota-carrying AEs
• Track record of meeting or exceeding revenue targets
• High EQ, excellent communication in French and English, and people-first leadership
• Expertise in outbound pipeline generation and consultative selling
• Experience navigating complex deals and multiple stakeholders
• Data-driven decision-making and sound business judgment
  
  

Please note that as we serve customers across Canada, bilingualism is essential for this position. You will be required to communicate in French and English.

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