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New Business Account Executive, Canada

Remote, USA Full-time Posted 2026-06-22

Tailscale is a company focused on building a secure and interconnected Internet for users of all sizes. They are seeking a New Business Account Executive to drive sales by managing inbound leads and sourcing new business opportunities, while becoming an expert in their services and supporting customers across all time zones.

Responsibilities

  • Become an expert in how Tailscale helps our customers
  • Win new business. Find your way to the right people at prospective customers, educate them about our services, and help them succeed with Tailscale
  • Experiment and move quickly. Analyze market landscapes and customer trends to inform your sales campaigns
  • Travel to (or organize) local events and attend large industry events to evangelize Tailscale to prospective customers
  • Support customers across all time zones
  • Manage and organize your activities, pipeline, and forecast in Gong and Salesforce

Skills

  • 1 or more years of closing experience in a door-to-door or in-person sales role
  • Ambition to build (and not just follow) a sales playbook
  • A technical background or curiosity in technology
  • Excellent communication and presentation skills
  • Proactive from lead to close
  • This role is based in Vancouver and is hybrid preferred (3 days/week in-office)

Benefits

  • An inclusive, flexible environment where you can be your authentic self.
  • A competitive total compensation package.
  • Comprehensive group benefits with no waiting period.
  • Remote first company—most of our teams work fully remotely.
  • Connect with other Tailscalars IRL.
  • Support for your personal and professional development.
  • Paid time off and a healthy work-life integration.
  • A build-your-own home office setup.
  • Generous parental leave program from your first day.

Company Overview

  • Tailscale is a software company that provides zero-configuration virtual private networks (VPNs) for secure connectivity. It was founded in 2019, and is headquartered in Toronto, Ontario, CAN, with a workforce of 201-500 employees. Its website is https://www.tailscale.com.
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