Sales Development Representative

Fleet Glass Services, Inc.; Toronto; Hybrid; CAD 55,000 - 85,000; Full time

Benefits offered by this job

Hybrid work

4 weeks vacation

Wellness days

Volunteer day

Coursera access

RRSP matching

Job summary

Dialogue is hiring a Sales Development Representative to open doors and fuel growth through creative, targeted outreach. You will research accounts, personalize messages, and collaborate with Account Executives to convert interest into booked meetings. You’ll leverage Salesforce, LinkedIn Navigator, and AI tools to improve efficiency.

You will be part of a hybrid team with in-person collaboration in Montreal or Toronto, contributing to Dialogue’s mission to transform virtual care in Canada.

Qualifications

• Experience in a sales, business development, or customer-facing role
• Bonus points if in SaaS, health, benefits, or insurance
• Curious about people and businesses and understanding what makes a prospect tick

Responsibilities

• Generating qualified opportunities through outbound prospecting across email, phone, LinkedIn, and other channels
• Researching target accounts to craft relevant, personalized outreach
• Leveraging AI tools to sharpen research and personalize outreach at scale
• Partnering with Account Executives and Marketing to build account strategies and convert inbound interest into meetings
• Keeping Salesforce clean and current so every lead, activity, and opportunity tells a story
• Testing new messaging, sequences, and channels and sharing insights with the team
• Conducting discovery to uncover pain points in employee wellness strategies and articulate Dialogue’s value

Skills

Sales experience

Customer-facing

Curious about people

AI in workflow

Tools

Salesforce

LinkedIn Navigator

Sales engagement platform

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].

AI Disclosure Statement

To ensure an efficient and fair review process, we utilize artificial intelligence tools to assist in the initial screening and assessment of applicants for this role. Dialogue only contacts candidates through official @dialogue.co email addresses. We never request payment, gift cards, or personal financial information at any stage of hiring, and we never extend an offer without a structured interview process. All open roles are listed exclusively at dialogue.co/en/careers. If you receive a suspicious communication claiming to be from Dialogue, do not respond — report it to [e-mail] and verify the role on our official careers page.

Your role asa Sales Development Representative

Reporting to Corey Klein, Director of Revenue Operations, the mission of the Sales Development Representative is to open doors that others can’t by bringing creativity, fearlessness, and genuine curiosity to every outreach, turning cold accounts into warm conversations that fuel Dialogue’s growth.

What you'll be doing

• Generating qualified opportunities through outbound prospecting across email, phone, LinkedIn, and other creative channels
• Researching target accounts to craft relevant, personalized outreach that resonates with each audience
• Leveraging AI tools to sharpen research, personalize outreach at scale, and work smarter, treating AI as a teammate that helps you punch above your weight
• Partnering closely with Account Executives and Marketing to build account strategies and convert inbound interest into booked meetings
• Keeping Salesforce clean and current so that every lead, activity, and opportunity tells a clear story
• Testing new messaging, sequences, and channels fearlessly, sharing what’s working (and what’s not) with the team to raise the bar for everyone
• Conducting discovery to uncover pain points and opportunities for enhancement in organizations employee wellness strategy, and effectively communicate Dialogue’s value as a potential solution
• Representing Dialogue’s mission authentically in every interaction, so prospects feel the difference from the very first touchpoint

We'd love to hear from you if you have

• You have some experience in a sales, business development, or customer-facing role (bonus points if it’s in SaaS, health, benefits, or insurance)
• You’re curious about people and businesses, and you enjoy figuring out what makes a prospect tick before reaching out
• You’re comfortable with tools like Salesforce, LinkedIn Sales Navigator, and sales engagement platforms, or you pick up new tools quickly
• You’re already experimenting with AI in your workflow, or you’re genuinely excited to
• You’re energized by targets and feedback, and you treat a “no” as information rather than rejection
• You like being in the details while never losing sight of the bigger goal, and you thrive collaborating with AEs, marketing, and RevOps to hit it

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