SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Salary: CAD 268,000 - 335,000 / annual
Tailscale is seeking a Sales Manager to lead the Commercial Expansion team (focused on existing customers with <750 employees) from their new Toronto sales hub. This is a hands-on leadership role where you'll build a repeatable sales machine from the ground up, managing a team of account executives while staying deeply involved in prospecting, customer relationships, and deal execution.
Key responsibilities include leading the team from the front—prospecting alongside AEs, conducting role plays, unblocking critical opportunities, and traveling to customers to build relationships. You'll establish best practices for pipeline generation, opportunity management, and customer relationship building. The Commercial segment balances high-velocity sales (7-13 opportunities per month) with occasional large deals ($50K–$100K+ ACV). You'll develop and coach the team using sales data and performance metrics, and collaborate closely with marketing, product, sales engineering, and partnerships to create pipeline and accelerate opportunities.
The role requires 1+ years of B2B SaaS sales management experience, excellent communication skills, ability to manage multiple activities simultaneously, and willingness to travel to industry events quarterly. This is a hybrid position requiring 3 days per week in-office in Toronto. Tailscale is a fully distributed, venture-backed company (backed by Accel, CRV, Insight, Heavybit, Uncork Capital) founded in 2019, building secure networking software on WireGuard that helps teams of all sizes protect networks and share access to internal tools.
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
