Lead commercial expansion sales at Tailscale from Toronto, coaching Account Executives and driving customer growth through structured sales execution.

As Tailscale’s first Toronto sales leader, you will establish the sales hub and manage Commercial Account Executives. You will hire talent, build an expansion motion, and help teams handle rapid-moving and complex deals. The work includes pipeline management, forecasting, and cross-functional partnership.

Key Responsibilities:

- Establish Tailscale’s Toronto sales hub and hire expansion Account Executives
- Drive expansion revenue, pipeline health, and accurate forecasting
- Prospect with representatives and support pivotal customer deals
- Coach through call reviews, role plays, and deal strategy




- Build repeatable playbooks using sales data and customer insights

Requirements:
- At least one year managing people in B2B SaaS sales
- Ability to coach and motivate quota-carrying sales professionals
- Understanding of prospecting, discovery, qualification, pipeline, and closing
- Data-driven approach to performance, coaching, and accountability
- Ability to work Toronto office three days weekly and travel quarterly

Shape Tailscale’s Toronto expansion team through coaching, forecasting, customer engagement, and repeatable commercial sales execution.

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📌 Commercial Expansion Sales Manager (Toronto)
🏢 Teli Labs
📍 Toronto