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Salary: CAD 201,000 - 201,000 / annual
Tailscale is a rapidly growing secure networking platform built on WireGuard, enabling teams to securely interconnect people and devices. As a Customer Account Executive, you will drive expansion and renewal of existing customer accounts, focusing on identifying additional use cases, educating clients on new features, and ensuring successful adoption across your portfolio.
You will own upsell and renewal revenue targets while building a credible quarterly pipeline. Key responsibilities include becoming an expert in Tailscale's value proposition, creating mutual action and success plans with customers, providing accurate forecasting, and collaborating closely with Solutions Engineering, Customer Success, Support, Marketing, and Product teams. Video-recorded customer meetings are a core part of the role, used for training and quality improvement.
You will manage multiple opportunities simultaneously at various stages, from evaluation through expansion and renewal. The role requires proactive engagement—the company encourages candidates to go beyond standard applications by researching and reaching out to hiring managers directly.
This is a hybrid position based in Toronto, requiring 3 days per week in-office. You'll work within a fully distributed, energetic company backed by top-tier investors including Accel, CRV, and Insight. The team emphasizes coaching, feedback, and collaboration to maximize performance and earning potential while aligning with customer needs.
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
