Commercial Expansion Sales Manager

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 fast-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 ExecutivesDrive expansion revenue, pipeline health, and accurate forecastingProspect with representatives and support pivotal customer dealsCoach through call reviews, role plays, and deal strategyBuild repeatable playbooks using sales data and customer insightsRequirements:
At least one year managing people in B2B SaaS salesAbility to coach and motivate quota-carrying sales professionalsUnderstanding of prospecting, discovery, qualification, pipeline, and closingData-driven approach to performance, coaching, and accountabilityAbility to work Toronto office three days weekly and travel quarterlyShape Tailscale’s Toronto expansion team through coaching, forecasting, customer engagement, and repeatable commercial sales execution.
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