Remote Sales Development Rep (SDR) Jobs in Canada 2026

Global B2B Insurance Partner

• Remote (Global)
• Nov 6, 2026

🌍 About SafetyWing We’re building simple, borderless health insurance for global teams. SafetyWing provides full health coverage for employees, contractors, and freelancers in 175+ countries under a single global plan.

Inbound Sales & Lead Management Virtual Assistant

• Remote (Global)
• Nov 3, 2026

APPLICATION INSTRUCTIONS: If you’ve already completed the 20four7VA Recruiting Process—including the Final Interview—or have previously been contracted by a 20four7VA Client, please make sure to apply via the 20four7VA Team Portal for faster processing.

Head of Sales Development

• Canada (Toronto only · CA: ON)
• $250,000 – $300,000/yr
• Nov 2, 2026

Marketing today runs on creative, and the teams winning right now treat it like a system instead of a guessing game. They research what’s working in the feed, figure out why, make more of it, and measure what happens.

Remote Outbound Callers: Ongoing Call Campaigns

• Remote (Global)
• $30/hr
• Nov 1, 2026

We're hiring motivated outbound callers to join our growing network for ongoing campaigns. This initiative helps us establish a reliable pool of remote talent to handle consistent calling volume. Your efforts directly feed into our continuous outreach strategies.

Appointment Setter (Enrollment Specialist)

• United Kingdom, North America
• From $24,000/yr
• Oct 8, 2026

As an Appointment Setter (Enrollment Specialist), you’ll be responsible for generating and qualifying opportunities, and booking high-quality sales calls for our Account Executives.

Sales Development Representative

• United States, Canada
• $53,000 – $75,000/yr
• Sep 23, 2026

GitLab is the intelligent orchestration platform for DevSecOps. GitLab enables organizations to increase developer productivity, improve operational efficiency, reduce security and compliance risk, and accelerate digital transformation.

Growth Outbound Sales Caller & Lead Qualification Specialist

• Remote (Global)
• Jul 17, 2026

APPLICATION INSTRUCTIONS: If you’ve already completed the 20four7VA Recruiting Process—including the Final Interview—or have previously been contracted by a 20four7VA Client, please make sure to apply via the 20four7VA Team Portal for faster processing.

Strategic Sales Development Representative

• United States, North America, Latin America (US: CO, MA)
• Up to $100k/yr
• Jun 9, 2026

Monte Carlo is the agent trust platform that autonomously observes, fixes, and continuously improves agents and the data that powers them — so enterprises can scale trust at the speed of AI.