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 ExecutivesDrive expansion revenue, pipeline health, and accurate forecastsProspect alongside reps and navigate complex customer opportunitiesCoach through call reviews, role plays, and deal sessionsBuild expansion playbooks using sales data and insightsRequirements:
At least one year managing B2B SaaS salespeopleExperience coaching quota-carrying Account ExecutivesUnderstanding of prospecting, discovery, qualification, and closingData-driven performance management and structured coaching experienceAbility to work Toronto office days weekly and travel quarterlyShape Tailscale’s commercial expansion engine through sales leadership, coaching, pipeline management, and customer-focused execution.
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📌 Commercial Expansion Sales Manager (Winnipeg)
🏢 WinsAbove
📍 Winnipeg