Lead commercial expansion sales at Tailscale from Toronto, coaching Account Executives and driving pipeline, forecasts, and customer growth.
As Tailscale’s first Toronto sales leader, you will manage Commercial Account Executives in a B2B SaaS workplace. You will build the sales hub, hire talent, and create a repeatable expansion motion. The work combines coaching, deal strategy, prospecting, and cross-functional partnership.
Key Responsibilities: Hire and onboard Commercial Expansion Account Executives
Drive expansion revenue, pipeline health, and accurate forecasts
Prospect alongside reps and navigate complex customer opportunities
Coach through call reviews, role plays, and deal sessions




Build expansion playbooks using sales data and insights
Requirements: At least one year managing B2B SaaS salespeople
Experience coaching quota-carrying Account Executives
Understanding of prospecting, discovery, qualification, and closing
Data-driven performance management and structured coaching experience
Ability to work Toronto office days weekly and travel quarterly
Shape Tailscale’s commercial expansion engine through sales leadership, coaching, pipeline management, and customer-focused execution.

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📌 Commercial Expansion Sales Manager (Ontario)
🏢 WinsAbove
📍 Ontario